Month: August 2021

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. 42265-67-8, name is 4-(tert-Butyl)-2-chloroaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 42265-67-8

a) 4-t-Butyl-2-chloroaniline (30 g) was dissolved in dichloromethane (1.21) and the solution was cooled to -5 C. N-Chlorosuccinimide (21.7 g) was added portionwise to the vigorously stirred solution and stirring was continued for 1 h. Dimethyl sulfide (36 ml) was added to the solution (-5 C.) and stirring was continued for a further 1 h. The solution was then cooled to -65 C. and triethylamine (27 ml) was added. This solution was evaporated to half volume, washed successively with sodium hydroxide (1N), water and brine. The organic solution was dried (MgSO4) and evaporated in vacuo and the residue was purified on silica using hexane to 3% ether in hexane as eluent. This afforded 4-t-butyl-2-chloro-6-(methylthiomethyl)aniline (31.2 g) as a red oil. 1 H NMR (250 MHz, CDCl3) delta1.27 (9H, s, (CH3)3, 1.99 (3H, s, SCH3), 3.69 (2H, s, CH2 SCH3), 4.38 (2H, brs, NH2), 6.92 (1H, d, J=2.0 Hz, Ar–H), 7.21 (1H, d, J=2.0 Hz, ArH). m/z (CI+)=244 (M+ +1, 100%).

According to the analysis of related databases, 42265-67-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Ltd.; US5633281; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 33863-76-2, The chemical industry reduces the impact on the environment during synthesis 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, I believe this compound will play a more active role in future production and life.

To a solution of ethyl 4-ethyl-3-hydroxyphenylacetate (12a, 0.700 g; 3.36 mmol) and NMP (8 mL) was added K2CO3 (1.393 g; 10.08 mmol) and 1-bromo-3-chloro-5-fluorobenzene (59b, 0.774 g; 3.7 mmol). The reaction was heated to 120 C. and monitored by TLC. After 8 h the reaction was cooled to RT and 10% HCl was added. The mixture was extracted with EtOAc and the combined extracts were washed with H2O and brine. The extracts were dried (Na2SO4) filtered and evaporated. The crude product was chromatographed with silica gel and eluted with a gradient of hexane/EtOAc (100 to 60% hexane) to afford 124a.

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, 1-Bromo-3-chloro-5-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Roche Palo Alto LLC; US2005/239881; (2005); A1;,
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. 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, A new synthetic method of this compound is introduced below., name: (4-Chloro-3-fluorophenyl)methanamine

4-{[(2,4-Dimethoxybenzyl)(l,3-thiazol-2-yl)amino]sulfonyl}-3-fluorobenzoic acid (Preparation 10, 75mg, 0.166mmol, leq), Et3N (36mg, 0.36mmol, 2.2eq), 2-(lH-benzotriazol- l-yl)-l,l,l,3,tetramethyluronium tetrafluoroborate (TBTU, 66mg, 0.206mmol, 1.24eq) and A- chloro-3-fluorobenzylamine (48mg, 0.301mmol, 1.81eq) were combined in THF (3ml) and the reaction mixture stirred at room temperature for 18 hours. The solvent was evaporated and the residue dissolved in DCM:TFA (2ml: 2ml), the reaction mixture was stirred at room temperature for 2 hours. Water (4ml) was added and the mixture was passed through a phase separation cartridge. The DCM was collected, washed with saturated sodium hydrogen carbonate, dried over sodium sulphate, filtered and evaporated in vacuo. The crude material was triturated with DCM then purified further by preparative HPLC to yield the title compound.[0358] LCMS Rt= 3.14-3.18 min. MS m/z 443 [MH]+

The synthetic route of 72235-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICAGEN, INC.; PFIZER LIMITED; WO2008/118758; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 3972-56-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under an argon atmosphere,4.2 mg (0.015 mmol) of dichlorobis (trimethylphosphine) nickel,83.8 mg (0.5 mmol) of 4-tert-butyl-1-chlorobenzene,152 mg (1.0 mmol) of cesium fluoride,140 mg (0.55 mmol) of 4,4,5,5,4 ‘, 4’, 5 ‘, 5′-octamethyl-2,2’-bi (1,3,2-dioxaborolanyl)180 mg (1.05 mmol) of trimethyl (2,2,2-trifluoroethoxy) silane and 0.5 mL of tetrahydrofuran were added and sealed,And the mixture was stirred at 100 C. for 12 hours.After the reaction vessel was cooled to room temperature, 1 mL of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted three times with 8 mL of ethyl acetate, and the obtained organic phases were combined.The solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography (hexane: chloroform: ethyl acetate = 16: 4: 0 to 16: 4: 1)2- (4-tert-butylphenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane93 mg (white solid, yield 72%) was obtained.

The synthetic route of 1-tert-Butyl-4-chlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH INSTITUTE; YAMAKAWA, TETSU; YAMAMOTO, TETSUYA; TAKAGI, JUN; (31 pag.)JP5699037; (2015); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, molecular formula is C3H4Cl3NO, 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. Recommanded Product: Methyl 2,2,2-trichloroacetimidate

Examples 24 – 273-(3,5-dibromo-4-{[2-isopropylcarbamoyl-lH-benzimidazol-5-yl]oxy}phenyl)-2- fluoropropanoic acid3-(3,5-dibromo-4-{[2-ethylcarbamoyl-lH-benzimidazol-5-yl]oxy}phenyl)-2-fluoropropanoic acid3-(3,5-dibromo-4-{[2-diisopropylcarbamoyl-lH-benzimidazoI-5-yl]oxy}phenyl)-2- fluoropropanoic acid 5-[2,6-Dibromo-4-(2-fluoro-2-isopropylcarbanioyl-ethyI)-phenoxy]-lH-benzoimidazoIe-2- carboxylic acid ^^Methyl 3-[4-(4-amino-3-nitrophenoxy)-3,5-dibromo-phenyl]-2-fluoro-propanoate (intermediate 10) (22 mg, 0.045 mmol) and platinum oxide (2.3 mg, 0.010 mmol) were suspended in ethyl acetate (2 mL), and hydrogenated under pressure (5 psi) for 15 h. The reaction mixture was filtered through a celite pad and concentrated, purified by flash chromatography (methanol/dichloromethane 0:10 to 5:5) to give 19 mg (92 % yield) of methyl 3-[4-(4,3-diamino-phenoxy)-3,5-dibromo-phenyl]-2- fluoro-propanoate.Methyl 3-[4-(4,3-diamino-phenoxy)-3,5-dibromo-phenyl]-2-fluoro-propanoate was dissolved in acetic acid (0.1 mL) and cooled to 0 0C, methyl trichloroacetimidate (Cl3CC(NH)OMe) (6 muL, 0.045 mmol) was added. The reaction was stirred for 1 h at room temperature. Water was added and the product was extracted with dichloromethane using a phase separator to give methyl 3-(3,5-dibromo- 4-{[2-trichloromethyl-lH-benzimidazol-5-yl]oxy}phenyl)-2-fluoropropanoate which was used in the next step without further purification.The crude methyl 3-(3,5-dibromo-4-{[2-trichloromethyl-lH-benzimidazol-5-yl]oxy}phenyl)-2- fluoropropanoate was dissolved in 1 mL of a stock solution (100 muL isopropylamine, 162muL triethylamine, 24 mL ethanol) and stirred at room temperature over night. Potassium hydroxide (2 mL, 2 M) was added and the stirring continued for 1 h. Hydrochloric acid (1 M, 10 mL) was added and the mixture was extracted into ethyl acetate (3 x 30 mL). The combined organic phases were dried, filtered and concentrated. The obtained residue was purified by semi-preparative-HPLC (Zorbax CombiHT (SB-C8 50×21.2 mm, 5mu). Mobile Phase: Solvent A. Water with 0.5 % formic acid; Solvent B: acetonitrile. Gradient: 2 min 80 % of A then over 8 min to 5% of A) to give 1 mg (5 % yield over 3 steps) of 3-(3,5-dibromo-4-{[2-isopropylcarbamoyl-lH-benzimidazol-5- yl]oxy}phenyl)-2-fluoropropanoic acid and also unexpected 1 mg of 3-(3,5-dibromo-4-{[2- ethylcarbarnoyl-l H-benzimidazol-5-yl]oxy}phenyl)-2-fluoropropanoic acid, 0.8 mg of 3-(3,5- dibromo-4-{[2-diisopropylcarbamoyl-lH-benzimidazol-5-yl]oxy}phenyl)-2-fluoropropanoic acid and 0.7 mg of 5-[2,6-Dibromo-4-(2-fluoro-2-isopropylcarbamoyl-ethyl)-phenoxy]-l H- benzoimidazole-2-carboxylic acid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2533-69-9, its application will become more common.

Reference:
Patent; KARO BIO AB; WO2007/128492; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 20850-43-5, These common heterocyclic compound, 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, 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.

General procedure: Suspension of the appropriate 3-amino-1,1-dioxo-1,4,2-benzodithiazine derivative 4a-h (0.5 mmol), anhydrous K2CO3 (1.5 mmol, 0.21 g) and the appropriate alkyl chloride (0.6 mmol) in dry THF (5 ml) was heated at reflux for 20-24 h, then cooled in ice-bath and filtered off. The crude product was suspended in 5 ml of water, heated gently to ca. 50 C; and cooled with vigorous stirring until granular precipitate appeared. Filtering off and washing with cold water and diluted EtOH gave pure potassium salts. 4.5.6 ;N-{2-[(1,3-Benzodioxol-5-yl)methylthio]-4-chloro-5-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]benzenesulfonyl}cyanamide potassium salt (5j) ;Starting from 4b (0.214 g) and 1,3-benzodioxol-5-ylmethyl chloride (0.102 g). Yield: 0.240 g (80%): m.p. 308-310 C; IR (KBr): nu 3436, 3086, 2924, 2172, 1602, 1585, 1543, 1502, 1486, 1327, 1289, 1253, 1141 cm-1; 1H NMR (500 MHz, DMSO-d6): delta 4.36 (s, 2H, SCH2), 6.01 (s, 2H, OCH2O), 6.88-7.04 (m, 5H, Ar), 7.68 (s, 1H, Ar), 7.70 (m, 2H, Ar), 8.08-8.09 (m, 2H, Ar), 8.47 (s, 1H, Ar); Anal. C23H13Cl2KN4O5S2 (C, H, N).

Statistics shows that 5-(Chloromethyl)benzo[d][1,3]dioxole is playing an increasingly important role. we look forward to future research findings about 20850-43-5.

Reference:
Article; Brozewicz, Kamil; Slawinski, Jaroslaw; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 384 – 394;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 932-32-1, 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. 932-32-1, name is 2-Chloro-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

Example 9-28; Compound 1 (80 mg) was suspended in methylene chloride (12 ml), and then thereto were added DMF (9 mul) and oxalyl chloride (94 mul), and the mixture was heated to reflux for an hour. The reaction solution was cooled, and then concentrated under reduced pressure. The residue was suspended in chloroform (18 ml), and then thereto was added Compound 2 (180 mul). The mixture was stirred at room temperature for 90 minutes. To the reaction mixture was added water, and the mixture was separated, and then the solvent of the organic layer was distilled away under reduced pressure. To the residue were added THF (5 ml), methanol (1 ml) and 1N-aqueous sodium hydroxide solution (550 mul), and the mixture was stirred at room temperature for an hour. The reaction mixture was diluted with ethyl acetate, and then washed with water and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent chloroform-ethyl acetate 50:50 to 0:100 gradient), and then the resulting solid was triturated by a mixed solvent of ethyl acetate-n-hexane to give Compound 3 (47 mg) as a colorless powder.MS (APCI) 343/345 [M+H]+

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

Reference:
Patent; Yamaguchi, Tetsuo; Ushirogochi, Hideki; Hirai, Miki; Imanishi, Yasuhiro; US2012/16117; (2012); A1;,
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. 363-51-9, name is 2-Chloro-6-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Chloro-6-fluoroaniline

To a solution of 2-chloro-6-fluoro aniline (3.0 g, 19.35 mmol) in DCM (10 mL), N- ethyl di-isopropyl amine (8.0 g, 64.00 mmol) was added. The reaction mass was stirred at RT for 30 minutes. The reaction mass was cooled at 0C and drop-wise thiophosgene (5.01 g, 43.47 mmol) was added to the reaction mixture. The reaction mass was stirred RT for 3-4 h. After completion of reaction, the reaction mass was diluted with DCM and purified by using column chromatography to afford 1.0 g of desired title product. 1H NMR (DMSO-d6): delta 7.26 (m, 2H), 7.06 (t, J= 9.6Hz, 1H).

According to the analysis of related databases, 363-51-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; DESHMUKH, Sanjay; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/153535; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13745-86-3, name is 11-Chlorodibenzo[b,f][1,4]thiazepine, 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 13745-86-3, Quality Control of 11-Chlorodibenzo[b,f][1,4]thiazepine

Example 8 1-piperazinyldibenzo[b,f][1,4]thiazepine A 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 45-50 C. To the resulting solution was added piperazine 73.0 (0.84 moles) at 45-50 C. The reaction mixture was heated to 70-80 C. The reaction mixture was maintained at 70 C. to 80 C. for 120-180 min. The reaction mixture was analyzed by HPLC (to check for absence of compound of formula III) and was cooled to 20 C. to 25 C. The reaction mixture was added 250 cc DM water and was stirred for 30 min. at 25-30 C. The layers were separated and the organic layer washed with 250 cc DM water. The organic phase was distilled off under vacuum below 70 C. 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 0-5 C. The reaction mass was filtered with the filtrate (mother liquor) containing 11-piperazinyldibenzo[b,f][1,4]thiazepine. Purity of 11-piperazinyldibenzo[b,f][1,4]thiazepine in toluene was more than 98.0% (area % by HPLC).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Kansal, Vinod Kumar; Ahmad, Suhail; Lal, Kanhaiya; Patil, Bhatu Tumba; US2008/241949; (2008); A1;,
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. 32943-25-2, name is 3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepine, A new synthetic method of this compound is introduced below., Safety of 3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepine

Example 11 2-(4-(3-(3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propyl)-1-piperazinyl)-3-pyridinecarboxylic acid dihydrochloride STR17 To a solution of 3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine (5.0 g, 22 mmol) in toluene (20 ml), 3-chloropropionyl chloride (3.32 g, 26 mmol) in toluene (8 ml) was added dropwise. The reaction mixture was stirred at 95 C. for 2 h and left stirring at room temperature overnight. 2 N Sodium hydroxide (25 ml) followed by toluene (50 ml) were added, and the phases were separated. The toluene phase was washed with 2 N sodium hydroxide (2*25 ml), water (3*30 ml) and brine (30 ml). The organic phase was dried (MgSO4) and evaporated in vacuo. The residue was stripped with methanol (30 ml) and the residue was suspended in ethyl acetate (8 ml), stirred and filtered off. The solid was washed with ethyl acetate (10 ml) and dried. This afforded 4.0 g (57%) of 3-chloro-1-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propan-1-one

The synthetic route of 32943-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novo Nordisk A/S; US5916889; (1999); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics