Tag: M.W=100-200

A common compound: 6940-78-9, name is 1-Bromo-4-chlorobutane, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 6940-78-9

After 7-hydroxy-lH-quinolin-2-one (10 g) and DMF (50 ml) were heated to approximately 30C, an aqueous potassium carbonate solution (potassium carbonate: 8.6 g, water: 10 ml) was added. After the mixture was stirred at 30 to 40C for about 15 minutes, l-bromo-4-chlorobutane (14.3 ml) was added and stirred at approximately 40C for 5 hours. Water (100 ml) was added dropwise over a period of 30 minutes or more while the temperature was maintained at 30C or more. After the mixture was stirred at approximately 30C for 30 minutes, stirring was continued at 10C or less for 1 hour, after which the precipitated crystals were collected by filtration. After methanol (100 ml) was added to the precipitated crystals, the mixture was stirred under reflux to ensure dissolution. This solution was cooled and stirred at 30 to 40C for 30 minutes and then at 5C or less for about 1 hour, after which the precipitated crystals were collected by filtration. The crystals were dried at 60C to obtain 7- (4-chlorobutoxy) -lH-quinolin-2-one as white powder. Yield: 12.3 g ^I-NMR (300 MHz; CDC13) oppm; 1.95-2.05 (4H, m) , 3.64 (2H, t, J = 6.0Hz), 4.10 (2H, t. J = 5.5 Hz), 6.56 (1H, d, J = 9.5 Hz), 6.80 (1H. dd, J = 9.0 Hz, 2.5 Hz), 6.84 (1H, d, J = 2.5 Hz), 7.45 (1H, d, J = 9.0 Hz), 7.73 (1H, d, J = 9.5 Hz), 12.45 (1H, brs).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 6940-78-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; SHINHAMA, Koichi; UTSUMI, Naoto; SOTA, Masahiro; FUJIEDA, Shigeo; OGASAWARA, Shin; WO2013/15456; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, molecular formula is C8H10ClN, 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. 13078-79-0.

General procedure: Compound 3 (0.37 g, 1 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (EDC, 0.29 g,1.5 mmol), 1-hydroxybenzotrizole (HOBT, 0.20 g, 1.5 mmol) and CHCl3 (20 mL) were stirred at roomtemperature for 1 h, and then different amines (3 mmol) were added. The solution was stirred atroom temperature overnight. Then the solvent was poured into water and extracted with ethylacetate (20 mL ¡Á 3). The solution was dried over anhydrous Na2SO4 and concentrated. The residues were purified by flash chromatography with chloroform/petroleum ether (2:1, v/v) elution.

The synthetic route of 2-(3-Chlorophenyl)ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Bo; Huang, Ai-Ling; Zhang, Yi-Long; Li, Zeng; Ding, Hai-Wen; Huang, Cheng; Meng, Xiao-Ming; Li, Jun; Molecules; vol. 22; 7; (2017);,
Chloride – Wikipedia,
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772-49-6, A common heterocyclic compound, 772-49-6, name is 1-Chloro-3-(trifluoromethoxy)benzene, molecular formula is C7H4ClF3O, 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.

To a cooed (-.78 C) souUon of 1-choro-3-(trfluoromethoxy)benzene (20 g, 102 mrno)n THF (100 mL) was added n-butyWthum (2.5 M/hexanes, 41 mL, 102 mmo) dropwseover a period of 10 minutes. Strrng was mantaned at -78C for I h, and then asouDon of odne (26 g, 102 rnrno) n THF (100 mL) was added dropwse at -.78 C overa perod of 30 ninutes. After the add Won, the temperature was niantaned at -78 C for1 h and then aflowed to warm to rt and stirred for a tota of 18 h. The reacton mixturewas poured nto saturated aqueous Na2SO3 and extracted wfth EtOAc (2 x 200 mL). The combined organc extracts were dried over Na2SO4 and concentrated n vacuo to give the tWe compound as an oH (28 g, 85% yed). 1H NMR (500 MHz, CDC3) oe 7.40 (dd, J = 81, 1.4 Hz, IH), 7.32 (t, J = 8.1 Hz, IH), 7.16 (dt, J = 8.2, 1.4 Hz, IH).

The synthetic route of 772-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; AMERIKS, Michael K.; RAVULA, Suchitra; SAVALL, Bradley M.; SWANSON, Devin M.; ZIFF, Jeannie M.; SHIREMAN, Brock T.; (167 pag.)WO2016/176463; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

932-96-7, Adding a certain compound to certain chemical reactions, such as: 932-96-7, name is 4-Chloro-N-methylaniline, 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 932-96-7.

General procedure: Sulfonyl chloride derivative 1 or 2 (3.99mmol) was added gradually to a mixture of substituted amine (4.39mmol) and pyridine (2mL) in EtOAc with stirring at 0C. The reaction mixture was stirred at room temperature until the TLC indicated complete conversion of the sulfonyl chloride to the sulfonamide intermediate. The reaction mixture was dissolved in DCM and extracted (2¡Á) with 10% NaOH. After the aqueous layer was acidified with 2N HCl, the precipitate was collected by filtration, washed with H2O, and dried in vacuo to give the desired products (5-22, 173, 174), which were carried forward without further purification.

According to the analysis of related databases, 932-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Khanfar, Mohammad A.; Quinti, Luisa; Wang, Hua; Choi, Soo Hyuk; Kazantsev, Aleksey G.; Silverman, Richard B.; European Journal of Medicinal Chemistry; vol. 76; (2014); p. 414 – 426;,
Chloride – Wikipedia,
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A common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, molecular formula is C3H4Cl3NO, 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. 2533-69-9.

2-Cyano-5-[2-chloro-4-(trifluoromethyl)phenoxy]-benzimidazole was prepared from 4-[2-chloro-4-(trifluoromethyl)phenoxy]-1,2-diaminobenzene as described below: To a solution of 4-[2-chloro-4-(trifluoromethyl)-phenoxy]-1,2-diaminobenzene (35 g; 0.122 mole) in acetic acid (165 ml), methyl trichloroacetimidate (15.1 ml; 0.122 mole) is added.

The synthetic route of Methyl 2,2,2-trichloroacetimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Agrochimie; US4622323; (1986); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

432-21-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 432-21-3 as follows.

1-Chloro-3-iodo-2trifluoromethyl-benzene; To a suspension of 3-Chloro-2-trifluoromethyl-phenylamine (121.61 g, 0.622 mol) in water (356 mL) was added 37% aqueous HCl portionwise allowing reaction temperature to rise to 42 C. The mixture was stirred for 30 minutes then cooled with ice/MeOH bath to 5 C. DCM (40 mL) was added and the mixture was stirred for 10 minutes. A solution of NaNO2 (53.52 g, 0.776 mol) in water (99 mL) was added dropwise while keeping the temperature of the reaction mixture below 5 C. After complete addition, the reaction mixture was stirred for 30 minutes and a solution of NaI (110.98 g, 0.740 mol) in water (198 mL) was added dropwise while keeping the temperature of the reaction mixture below 5 C. After completion of the addition, the reaction mixture was stirred for 1 hour and 15 minutes, and DCM (0.79 L) was added followed by NaHSO3(35.92 g) to discharge iodine color. The organic layer was washed (brine), and the water layer was sequentially reextracted (2¡Á0.2 L DCM). The organic layers were dried (Na2SO4), combined, and the volatiles were evaporated. The residue (180.55 g) was purified on 0.8 kg of silica gel (elution with 4 L of cyclohexane). The fractions were analyzed by GC, and those having more than 80% of the product were combined, and the volatiles were evaporated. The liquid residue was placed in the freezer for 1 hour, after which the solids were filtered, washed (pentane) and air-dried to afford 78.84 g (41%) of the desired product as beige solid in several crops (97-98% GC purity with 1H and 19F NMR’s clean and consistent with the desired product). The mother liquors were purified on 0.8 kg of silica gel (eluting with 4 L of cyclohexane). The fractions were analyzed by GC, and those having more than 80% of the product were combined and the volatiles were evaporated. The liquid residue was placed in the freezer for 1 hour, and solids were filtered, washed (pentane), and air-dried to give an additional 31.56 g (17%) of the 1-Chloro-3-iodo-2-trifluoromethyl-benzene as white solid (96% GC purity with 1H and 19F NMR’s clean and consistent with the desired product). Also, additional product was obtained (14.30 g, 8%, 81% pure GC) from mother liquors and 28.82 g (50% by GC, froim the less pure fractions. GC analysis done on a DB5 Column, 30 meters, 0.32 mm id, 0.25 um film, 75-300 C., 15 C./min., Injector temperature: 275 C., Detector temperature: 350 C., Retention time: 3.88 minutes. MS: APCl: M+: 306.0 (305.9)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 432-21-3, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; US2008/167319; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

29671-92-9, Name is Carbamimidic chloride hydrochloride, 29671-92-9, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Example 320 Synthesis of 2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one A mixture of ethyl 2-amino-5-(4-fluorophenyl)thiophene-3-carboxylate (0.3 g, 1.13 mmol), chloroformamidine hydrochloride (0.33 g, 2.83 mmol) and dimethylsulfone (0.53 g, 5.65 mmol) was heated at 120-130 C. for 30 minutes. After cooling down to room temperature, water (10 ml) was added and ammonium hydroxide was used to neutralize the suspension. The solid was filtered off, washed with water and dried. The crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 10:1) to yield the title compound as a white solid (0.28 g, 95%). 1H NMR (300 MHz, DMSO, 25 C.): delta=11.05 (s, 1H, NH), 7.66-7.71 (m, 2H, PhH), 7.51 (s, 1H, CH), 7.23 (t, J=8.8 Hz, PhH), 6.73 (s, 2H, NH2) ppm. HRMS: calcd for C12H9FN3OS 262.04504, found 262.04413.

Statistics shows that Carbamimidic chloride hydrochloride is playing an increasingly important role. we look forward to future research findings about 29671-92-9.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; De Jonghe, Steven; Gao, Ling-Jie; Herdewijn, Piet; Herman, Jean; Jang, Miyeon; Leyssen, Pieter; Louat, Thierry; Neyts, Johan; Pannecouque, Christophe; Vanderhoydonck, Bart; US2013/190297; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

39885-50-2, A common compound: 39885-50-2, name is 2-Chloro-4-(trifluoromethyl)aniline, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

(b) raney Nickel (0.7 g) was added to a solution of the above isomer mixture (35.85 g) in ethanol in a hydrogenation reactor at 50¡ã C. under hydrogen at 5 bar for 5 hours.. The mixture was cooled, filtered and evaporated to give a 95/5 mixture of 2-chloro-4-trifluoromethylaniline and 2-chloro-5-trifluoromethylaniline (33.1 g).. hydrogen chloride gas was added over 0.5 hour to a solution of the above mixture in ethanol and chlorobenzene, cooled to 0¡ã C., and filtered to give 2-chloro-4-trifluoromethylaniline hydrochloride (33.5 g), having a purity of >99percent.. The overall yield from 3,4-dichlorobenzotrifluoride was 85percent.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Chloro-4-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Aventis CropScience, S.A.; US6410737; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

15205-15-9, These common heterocyclic compound, 15205-15-9, name is 2-Chloro-6-fluorobenzylamine, 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.

Step 1: (S) -tert-Butyl (1- (4- ( (2-chloro-6-fluorobenzyl) carbamoyl) -2- (3-ethoxy-4-methoxyphenyl) oxazol-5-yl) ethyl) carbamate[0639]To 10 mL of dichloromethane were added (S) -5- (1- ( (tert-butoxycarbonyl) amino) ethyl) -2- (3-ethoxy-4-methoxyphenyl) oxazole-4-carboxylic acid (0.3 g, 0.74 mmol) , 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (212 mg, 1.11 mmol) and 1-hydroxy-7-azabenzotriazole (151 mg, 1.11 mmol) , and the mixture was stirred at 0 for 30 minutes. To the mixture were added dropwise (2-fluoro-6-chlorophenyl) methanamine (0.11 mL, 0.89 mmol) and N, N-diisopropylethylamine (0.39 mL, 2.21 mmol) in turn, and the resulting mixture was stirred at rt for 12 hours. The reaction mixture was washed with water (10 mL ¡Á 3) , and the organic layer was dried over anhydrous sodium sulfate. The organic solvent was removed and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) 6/1) to give the title compound as a white solid (190 mg, 47) .[0640]1H NMR (400 MHz, CDCl3) : delta ppm 7.60 (dd, J1 8.4 Hz, J2 1.9 Hz, 1H) , 7.52 (d, J 1.8 Hz, 1H) , 7.39 -7.29 (m, 1H ) , 7.27 -7.25 (m, 1H) , 7.10 -7.05 (m, 1H) , 6.94 (d, J 8.5 Hz, 1H) , 5.30 -5.25 (m, 1H) , 4.91 -4.84 (m, 2H) , 4.23 -4.18 (m, 2H) , 3.95 (s, 1H) , 1.57 -1.51 (m, 6H) , 1.45 (s, 9H) and MS-ESI: m/z 549.2 [M+H]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 15205-15-9.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; YU, Tianzhu; ZHANG, Yingjun; ZHANG, Xiangyu; ZHANG, Shiguo; CHENG, Changchung; ZHANG, Jiancun; WO2015/161830; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2533-69-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2533-69-9 name is Methyl 2,2,2-trichloroacetimidate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step D4-bromo- 6-cyclopropyl-2-(trichlorom ethyl)- 1 H-benz imidazole[00176] A suspension of (2-amino-3-bromo-5-cyclopropylphenyl)amine (11 .16 g, 42.3 mmol) in acetic acid (123 ml) followed by the drop-wise addition of methyl 2,2,2- trichloroethanimidoate (6.42 ml, 50.8 mmol). The mixture was stirred at room temperature overnight. The suspension was treated by additional methyl 2,2,2,-trichloroethanimidoate (3.0 mL) and stirred for 2 hours. The mixture was diluted with Et20 and treated with water and the layers were separated. The aqueous layer was extracted with Et20 (3x) and then the combined organic phase was washed with water (2 x), brine (2x), dried Na2S04, filtered, and concentrated. The residue was co-evaporated with toluene (2x) to give a brownish-black residue. The residue was triturated with Et20 and then solids were filtered and discarded. The filtrate was concentrated and then co-evaporated from toluene (2x) to give the title compound (8.44 g, 46.7%). ES-LCMS: 355.0, 357.0 (M+1 ).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2,2,2-trichloroacetimidate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna; CATALANO, John G; FANG, Jing; PEAT, Andrew James; TAI, Vincent; TURNER, Elizabeth; WO2011/97491; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics