Category: chlorides-buliding-blocks

Synthetic Route of 2533-69-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Preparation of 2-methyl-6-nitro-2H-indazole (5d). To a stirred mixture of 6-nitro-1H-indazole (1.0 g, 0.0061 mmol) in dichloromethane (25.0 mL) was added trifluoromethanesulfonic acid (0.54 mL, 0.0061 mmol), stirred for 5-10 min at 25-35 C. To this mixture was added methyl 2,2,2,-trichlroacetimidate (2.69 g, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16-18 h under N2. After reaction completion, chilled saturated NaHCO3 solution was added. The aqueous and organic phases were separated. Aqueous phase was extracted with dichloromethane 10 mL. Combined organic layers were washed with DM water (2 × 10 mL). Organic layer was dried over anhydrous Na2SO4, filtered, and evaporated completely under vacuum to obtain 2-methyl-6-nitro-2H-indazole (1.03 g, 95.0%) as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis Methyl 2,2,2-trichloroacetimidate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Baddam, Sudhakar Reddy; Uday Kumar; Panasa Reddy; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 54; 13; (2013); p. 1661 – 1663;,
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Electric Literature of 6579-54-0,Some common heterocyclic compound, 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, molecular formula is C6H3Cl3O2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a mixture of corresponding 7 (150mg, 0.4mmol) in anhydrous THF (15mL) and DMF(3mL), corresponding sulfonyl chloride (0.5mmol) was added slowly at 0C and stirred at room temperature overnight. The mixture was poured into water and extracted with ethyl acetate (50mL×3). The combined organic layer was washed by saturated sodium chloride solution (40mL×3) and concentrated. The residue was purified by silica gel chromatography to afford 8a-8i.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Dichlorobenzenesulfonyl chloride, its application will become more common.

Reference:
Article; Zhang, Li; Zhang, Beichen; Zhao, Jingyun; Zhi, Yanle; Wang, Lu; Lu, Tao; Chen, Yadong; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 942 – 951;,
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Application of 2106-04-9, A common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Preparation 19. 1-Methyl-4- (3-chloro-2- fluorophenylamino) piperidine; Combine 3-chloro-2-fluoroaniline (4. 37 g, 30 mmol), 1-methylpiperidin-4-one (3.39 g, 30 mmol), sodium triacetoxyborohydride (5.26 g, 33 mmol), and acetic acid (5.4 g, 90 mmol) and stir at room temperature overnight. Partition the reaction mixture between dichloromethane and saturated aqueous NaCl containing NH40H, dry over anhydrous sodium sulfate, evaporate and purify on a silica gel columnn (110 g), using a gradient of dichloromethane-2M NH3 in methanol to give 2.34 g of the title compound (32% yield): mass spectrum (ion spray): m/z = 243 (M+1) ; 1H NMR (CDC13) : 6.88 (ddd, lH), 6.63 (ddd, 1H), 6.56 (dd, 1H), 3.85 (br d, 1H), 3.28 (m, 1H), 2.80 (m, 2H), 2.30 (s, 3H), 2.13 (m, 2H), 2.04 (m, 1H), 1.53 (m, 2H). (file: mn4-b6k-284-2)

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/35499; (2005); A1;,
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Electric Literature of 6940-78-9, A common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

7.16 g of 7-hydroxy-2-quinolinone, 51.5 g of 1-bromo 4-chlorobutane, 37.32 g of potassium carbonate and4.18g of ethoxyformylmethylenetriphenylphosphine dissolved in 170mL of acetone, reacted at 45 C for 2.5h,After the reaction, 100 ml of a saturated sodium chloride solution was added, followed by extraction with ethyl acetate.The ethyl acetate extract was washed successively with saturated sodium chloride solution and deionized water.Dry over anhydrous sodium sulfate, concentrate under reduced pressure and dried in vacuo.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Wuhan Xing Hua Knowledge Pharmaceutical Technology Co., Ltd.; Lu Shan; Chen Jingrun; Zhang Chuantao; (16 pag.)CN109988162; (2019); A;,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 108-37-2, name is 1-Bromo-3-chlorobenzene, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 108-37-2, Application In Synthesis of 1-Bromo-3-chlorobenzene

A mixture of 3-bromo-l-chlorobenzene (191 mg, 1.0 mmol), 2,5- diazabicyclo [2.2.1]heptane-2-carboxylic acid tert-butyl ester (240 mg, 1.2 mmol), sodium tert-butoxide (135 mg, 1.4 mmol), Pd2 (dba)3 mg, 0.03 mmol), and BINAP (56 mg, 0.09 mmol) in toluene (3 mL) was heated to 110 C for 15 h. After cooling to room temperature, the mixture was filtered through celite, and the filter cake was rinsed with ethyl acetate. The solvents were removed in vacuo. Column chromatography on silica (hexanes: ethyl acetate 4: 1) of the residue afforded 5-(3-chlorophenyl)-2,5- diazabicyclo [2.2.1]heptane-2-carboxylic acid tert-butyl ester (240 mg, 78% yield) as a yellow solid. ¹H NMR (400 MHz, CDC13, mixture of rotamers) 8 7.10 (q, 1H), 6.65 (d, 1H), 6.50 (m, 1H), 6.40 (d, 1H), 4.62 (s, 0.5H), 4.48 (s, 0.5H), 3.53 (m, 1H), 3.47-3.67 (m, 2H), 3.20-3.08 (dd, 1H), 1.98-1.91 (m, 2H), 1.45 (s, 4.5H), 1.41 (s,

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-chlorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; EXELIXIS, INC.; WO2005/117909; (2005); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 13745-86-3, name is 11-Chlorodibenzo[b,f][1,4]thiazepine, A new synthetic method of this compound is introduced below., Recommanded Product: 13745-86-3

A 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of 11-chlorodibenzo [b,fj[l,4]thiazepine in toluene 350 cc [52 gm (0.22 moles)], and was added 73.0 gm (0.84 moles) of piperazine at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 70C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC. The reaction mixture was cooled to at 20C to 25C and was added 250 cc DM water and was stirred for 30 min. at 25-30C. The layers were separated and the organic layer washed with 250 cc DM water. The organic layer was forwarded for the next step. Purity of 11- piperazinyldibenzo [b,fj-[l,4] -thiazepine in toluene was more than 97% (area % by HPLC).Example 5. ll-piperazinyldibenzo[b,fl[l,41 thiazepineA 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of l l-chlorodibenzo[b,fj[l,4] thiazepine in toluene [52 gm (0.22 moles)], and was added 73.0 gm (0.84 moles) of piperazine at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 700C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC (to check for absence of compound of Formula III). The reaction mixture was cooled to at 20C to 25C was added 250 cc DM water and was stirred for 30 min. at 25-30C. The layers were separated and the organic layer washed with 250 cc DM water. To the organic phase was added 250 cc water and was acidified with formic acid to obtain a pH of 2-3. The contents were stirred for 15 min. and the layers were separated. The aqueous layer was washed with 150 cc toluene and the aqueous layer was basified with sodium carbonate to a pH of 8 to 10 and extracted with 3x 250 cc of toluene. Combine the organic layer and washed with DM water 130 cc twice. Purity of 1 l-piperazinyldibenzo[b,f][l,4] thiazepine in toluene was more than 99 % (area % by HPLC). Example 6. 11- piperazinyldibenzo fb,f|-[l.,41 -thiazepineA 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of 11-chlorodibenzo [b,fj[l,4] -thiazepine in toluene [52 gm (0.22 moles)], and the mixture was stirred for 15 min 45-50C.The resulting solution was added piperazine 73.0 gm (0.84 moles) at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 7O0C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC (to check for absence of compound of Formula III). The reaction mixture was cooled to 20C to 25C, to which, was added 250 cc DM water and was stirred for 30 min. at 25-300C. The layers were separated and the organic layer washed with 250 cc DM water. To the organic phase was added 250 cc water and it was acidified with acetic acid to obtain a pH of 2-3. The contents were stirred for 15 min. and layers were separated. The aqueous layer was washed with 150 cc toluene and the aqueous layer was basified with sodium carbonate to a pH of 8 to 10 and extracted with 3x 250 cc of toluene. Combine the organic layer and washed with DM water 130 cc twice. Purity of 11- piperazinyldibenzo [b,fj-[l,4] -thiazepine in toluene was more than 99 % (area % by HPLC); A 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of l l-chlorodibenzo[b,f][l,4] thiazepine in toluene [52 gm (0.22 moles)], and the mixture was stirred for 15 min 45-50C. To the resulting solution was added piperazine 73.0 (0.84 moles) at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 70C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC (to check for absence of compound of formula III) and was cooled to 20C to 25C. The reaction mixture was added 250 cc DM water and was stirred for 30 min. at 25-30C. The layers were separated and the organic layer washed with 250 cc DM water. The organic phase was distilled off under vacuum below 70C. Traces of toluene were removed by adding n-butanol. To the resultant oily mass was added 150 cc n-butanol. The mixture was stirred for 24 hrs and chilled to 0-5C. The reaction mass was filtered with the filtrate (mother liquor) containing 11-piperazinyldibenzo [b,fj [l,4]thiazepine. Purity of 11- piperazinyldibenzo[b,fj [1,4] thiazepine in toluene was more than 98.0% (area % by HPLC).Example 9. llpiperazinyldibenzo[b,fl [1,41 thiazepineA 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of 11 -chlorodibenzo [b,f][ 1,4] thiazepine in toluene [52 gm (0.22 moles)], and the mixture was stirred for 15 min 45-50C. To the resulting solution was added piperazine 73.0 gm (0.84 moles) at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 7O0C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC and was cooled to 20C to 25C. To the reaction mixture was added 250…

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2008/121415; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2106-04-9, name is 3-Chloro-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2106-04-9

Step 6. Preparation of N’-(3-chloro-2-fluoro-phenyl)-N,N-dimethyl-formamidine (compound (XII)).; 3-chloro-2-fluroaniline (5.30 g, 35.29 mmoles) was dissolved in 2- methyltetrahydrofuran (52.94 g). To this N,N-dimethylformamide dimethyl acetal (6.07 g, 49.41 mmoles) and acetic acid (0.11 g, 1.76 mmoles) were added. The resulting reaction mixture was heated, with stirring, to 76 0C for 3 hours. Following this the solvent was removed in vacuo at 400C to give compound (XII) as a yellow oil (6.60 g, 93% yield); IH NMR Spectrum (400 MHz, DMSO-d6) delta ppm 2.74 (s, 0.29H), 2.89 (s, 0.31H), 2.94 (s, 2.75H), 3.03 (s, 2.66H), 3.34 (br s, 0.70H), 5.48 (s, 0.06H) 6.91-7.10 (m, 3H), 7.79 (s, 1 H), 7.96 (s, 1 H). The NMR data above includes signals for N,N-dimethylformamide dimethyl acetal which is present in a 0.06 molar equivalence. The signals pertaining to N5N- dimethylformamide dimethyl acetal are at delta ppm shifts of 3.75, and 6.90-6.95. The signal at delta ppm 3.35 is due to residual water. Mass Spectrum (by LCMS EI): m/z (M+H)+ 201.2.

According to the analysis of related databases, 2106-04-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BOARDMAN, Kay, Alison; CUNNINGHAM, Oliver, Robert; GOUNDRY, William; LAFFAN, David, Dermot, Patrick; WO2010/122340; (2010); A2;,
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Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2401-24-3,Some common heterocyclic compound, 2401-24-3, name is 2-Chloro-5-methoxyaniline, molecular formula is C7H8ClNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

3-bromo-2-(trifluoromethyl)pyridine (0.4 g, 1.770 mmol), 2-(Dicyclohexylphosphino)-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (0.063 g, 0.133 mmol), Cesium carbonate (0.692 g, 2.124 mmol) and Palladium (II) Acetate (0.020 g, 0.088 mmol) were added to a microwave vial. Then, 2-chloro-5-methoxyaniline (0.293 g, 1.858 mmol) was added. The vial was purged with argon repeatedly. Dry toluene was added. The reaction was heated to 100 C. for 15 hours. The reaction mixture was filtered through celite, concentrated en vacuo. Normal phase chromatography (ethyl acetate/hexanes) was used to purify the crude material to give N-(2-chloro-5-methoxyphenyl)-2-(trifluoromethyl)pyridin-3-amine (0.376 g, 1.242 mmol, 70.2% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-5-methoxyaniline, its application will become more common.

Reference:
Patent; OssiFi Inc.; Ellies, Debra; Rey, Jean-Philippe; Kimball, F. Scott; US2014/288068; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 445-13-6, name is 3-Chloro-4-(trifluoromethyl)aniline, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 445-13-6, Safety of 3-Chloro-4-(trifluoromethyl)aniline

General procedure: To a solution of ethyl 4-bromo-1H-indole-2-carboxylate in toluene underargon atmosphere was added Pd2(dba)3 (0.1 eq), DavePhos (0.2 eq), K3PO4 (3 eq, 1Maqueous solution) and aryl amine (3 eq), and then the mixture was reacted at 80 Cuntil the starting material disappeared. The mixture was cooled to room temperatureand concentrated. Ethyl acetate was added to dissolve the residue and the mixture waswashed with saturated brine and water, dried over anhydrous Na2SO4, andconcentrated in vacuo. The crude product was purified by column chromatography toafford the target compound. Compounds 8a-8f, 8i-8l, 8a-1, 8a-6 ~ 8a-11, 8a-14 wereprepared with method 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Article; Cui, Guonan; Lai, Fangfang; Wang, Xiaoyu; Chen, Xiaoguang; Xu, Bailing; European Journal of Medicinal Chemistry; vol. 188; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 4090-55-5, HPLC of Formula: C5H10ClO3P

Synthesis Example 1 (Synthesis of Phosphorus Compound 1) (Reaction); In a four-necked 1-L flask provided with a stirrer, a thermometer, a dropping device, a hydrochloric-acid-absorber device and a condenser, 104.0 g (1 mole) of neopentyl glycol and 114.4 g of chlorobenzene were fed. The resulting mixture was heated at 45 to 55 C while stirring and 153.5 g (1 mole) of phosphorus oxychloride were dropwise added to the mixture in an hour. After addition, the mixture was heated to 75 C in an hour, and then was allowed to react at the same temperature (75 C) for an hour and 65.7 g of generated hydrogen chloride were recovered. Thereafter, the mixture was depressurized at the same temperature (75 C) and 26.6 kPa for 2 hours and remaining hydrogen chloride was absorbed as a gas. As a result, 298.9 g of the reaction mixture were obtained. The purity of the reaction mixture was found to be 95.6 area % by GPC (gel permeation chromatography). The resulting reaction mixture was cooled to room temperature to which 161.5 g (0.95 mole) of 2-phenylphenol (ortho-phenylphenol), 0.9 g of magnesium chloride and 145.6 g of chlorobenzene were added. The mixture was heated at 65 to 75 C while stirring and 106.1 g (1.05 moles) of triethylamine were dropwise added to the mixture in an hour. Thereafter, the mixture was allowed to react at the same temperature (75 C) for an hour and thereby obtaining a mixture of 5, 5-dimethyl-2-(2′-phenylphenoxy)-1, 3, 2-dioxaphosphorinane-2-oxide.(After-treatment) The obtained mixture was neutralized at 85 C by adding hydrochloric acid solution which corresponds to an excess amount of triethylamine and the mixture was allowed to stand to separate an oil phase. Next, the obtained oil phase was washed with approximately 85 C water and then dehydrated. The obtained oil phase was gradually cooled and 259.8 g of white needle-like crystals were crystallized out from the oil phase. The purity of the obtained crystals was found to be 99.0 area % by GPC. Also, if all of the crystals were assumed to be an object compound, the crude yield was 86.0 %. A structure of the obtained crystals was determined according to results of quantitative analysis of phosphorus by elemental analysis and absorption spectrometry using an UV spectrometer, 1H-NMR, 13C-NMR and FT-IR. The crystals were identified as 5, 5-dimethyl-2-(2′-phenylphenoxy)-1, 3, 2-dioxaphosphorinane-2-oxide (phosphorus compound 1) of the below-mentioned constructional formula. Also, a melting point of the crystal was measured by a microdose melting point apparatus (model number: MP-J3, manufactured by Yanaco Co., Ltd.). Quantitative analysis of phosphorus by elemental analysis and absorption spectrometry (theoretical values in parentheses): Carbon: 64.3 % (64.2 %) Hydrogen: 5.9 % (6.0 %) Phosphorus: 9.7 % (9.7 %) Melting point: 127 to 130 CIR (KBr): 2992, 2352, 1584, 1514, 1485, 1430, 1373, 1306, 1251, 1104, 1158, 1120, 1050, 1004, 980, 947, 922, 877, 701, 624 cm-1 2992, 2352, 1584, 1514, 1485, 1430, 1373, 1306, 1251, 1104, 1158, 1120, 1050, 1004, 980, 947, 922, 877, 701, 624 cm-1 NMR: 1H-NMR (CDCl3; 300MHz); delta 7.71 (1H, d, J=8Hz, o-PP), 7.55-7.26 (8H, m, o-PP), 3.62 (1H, d, J=10Hz, POCH2C(CH3)2-), 3.53 (2H, dd, JHH=10Hz, POCH2C(CH3)2-), 3.48 (1H, d, JHH=10Hz, POCH2C(CH3)2-), 1.17 (3H, s, POCH2C(CH3)2-), 0.42 (3H, s, POCH2C(CH3)2-) ppm1H-NMR (CDCl3; 300MHz); delta 7.71 (1H, d, J=8Hz, o-PP), 7.55-7.26 (8H, m, o-PP), 3.62 (1H, d, J=10Hz, POCH2C(CH3)2-), 3.53 (2H, dd, JHH=10Hz, POCH2C(CH3)2-), 3.48 (1H, d, JHH=10Hz, POCH2C(CH3)2-), 1.17 (3H, s, POCH2C(CH3)2-), 0.42 (3H, s, POCH2C(CH3)2-) ppm13C-NMR (CDCl3; 75MHz); delta 146.9 (d, 2JPC=6Hz), 137.3, 132.7 (d, 3JPC=7Hz), 130.9, 129.6, 129.0, 128.2, 127.6, 125.2, 120.4 (d, 3JPC=2Hz) (o-PP), 77.6 (d, 2JPC=7Hz, POCH2C(CH3)2-), 31.5 (d, 2JPC=6Hz, POCH2C (CH3)2-), 21.6, 19.5 ppm

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, and friends who are interested can also refer to it.

Reference:
Patent; DAIHACHI CHEMICAL INDUSTRY CO., LTD.; EP1925622; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics