Category: chlorides-buliding-blocks

13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, 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. 13918-92-8

General procedure: Compound 11a (800 mg,2.0 mmol) was dissolved in 10 ml ethyl acetate and then 9 N HCl(5 ml) was added, the reaction mixture was stirred for 30 min at roomtemperature, the reaction solvent was neutralized by NaHCO3 topH=8, 50 ml ethyl acetate and 30 ml H2O was added, after stirredadequately, the organic layer was separated, and concentrated, andthen the crude product was purified by silica gel columnchromatography using a mixture solvent of dichloromethane:methanol (20:1), to give white powder (540 mg); Above whitepowder (150 mg, 0.5 mmol) was dissolved in THF (10 ml),iodomethane (107 mg, 0.75 mmol) and triethylamine (0.5 ml) wereadded in the solvent. After the reaction mixture was stirred for 1 h at room temperature, the solvent was concentrated, the residues was purified by silica gel column chromatography using a mixture solvent ofdichloromethane: methanol (40:1), to give (12aa) Yield 49%, White powder.

Statistics shows that 13918-92-8 is playing an increasingly important role. we look forward to future research findings about 2,4-Difluorobenzene-1-sulfonyl chloride.

Reference:
Article; Zhang, Min; Jiang, Li; Tao, Jia; Pan, Zhaoping; He, Mingyao; Su, Dongyuan; He, Gu; Jiang, Qinglin; Bioorganic and Medicinal Chemistry; vol. 27; 11; (2019); p. 2268 – 2279;,
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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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., 202197-26-0

A stirred suspension of 3H-6-iodoquinazolin-4-one (compound A) in toluene (5 vols) was treated with tri-n-butylamine (1.2 eq.) at 20 to 25C, then heated to 900C. Phosphorous oxychloride (1.1eq) was added, the reaction mixture was then heated to reflux. The reaction mixture was cooled to 500C and toluene (5vols) added. Compound C (1.03 eq.) was added as a solid, the slurry was warmed back to 900C and stirred for 1 hour. The slurry was transferred to a second vessel; the first vessel was rinsed with toluene (2vol) and combined with the reaction mixture. The reaction mixture was cooled to 7O0C and 1.0 M aqueous sodium hydroxide solution (16 vols) added dropwise over 1 hour to the stirred slurry maintaining the contents temperature between 68-72C. The mixture was stirred at 65-700C for 1 hour and then cooled to 200C over 1 hour. The suspension was stirred at 200C for 2 hours, the product collected by filtration, and washed successively with water (3 x 5 vols) and ethanol (IMS, 2 x 5 vols), then dried in vacuo at 50-600C. Volumes are quoted with respect of the quantity of Compound A used. Percent yield range observed: 90 to 95% as white or yellow crystals.

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Reference:
Patent; SMITHKLINE BEECHAM (CORK) LIMITED; WO2006/26313; (2006); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 13726-14-2, name is 4-Chloro-3-methoxyaniline, I believe this compound will play a more active role in future production and life. 13726-14-2

This was prepared from 2,4-dichloro-5-iodopyrimdine(0.550 g) and 3-methoxy-4-chloroaniline (0.315 g) using procedure B (reaction time, 1 h) to give the title compound as a gray solid (0.708 g, 90%). Mp: 190-192 C (dec). lH NMR (400 MHz, DMSO-ifc): delta 8.94 (s, 1H, disappeared on D20 shake ), 8.59 (s, 1H), 7.43 (d, / = 2.3 Hz, 1H), 7.41 (d, / = 8.6 Hz, 1H), 7.21 (dd, / = 8.6, 2.3 Hz, 1H), 3.84 (s, 3H). HPLC-MS (ESI+): m/z 397.9 [78%, (M35C137C1+H)+], 395.9 [100%, (M35C135C1+H)+].

The chemical industry reduces the impact on the environment during synthesis 13726-14-2. I believe this compound will play a more active role in future production and life.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); A1;,
Chloride – Wikipedia,
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363-51-9, 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. 363-51-9, name is 2-Chloro-6-fluoroaniline, A new synthetic method of this compound is introduced below.

A solution of 5 -(2-(3,4-dimethoxyphenyl)propan-2-yl)-l -(4-fluorophenyl)- IH- imidazole-2-carbaldehyde (280 mg, 0.76 mmol), 2-chloro-6-fluoroaniline (332 mg, 2.28 mmol), TsOH (72 mg, 0.38 mmol) in THF (8 mL) was heated at reflux for 15 h over molecular sieves (4A). The solution was cooled to 0 0C, and NaBH4 (57 mg, 1.5 2mmol) was added in several portions. The resulting mixture was stirring for 1 h, and filtered through Celite to remove molecular sieves. The filtrate was quenched with H2O (5 mL), 2N NaOH (5 mL) and extracted with DCM (2 x 10 mL). The organic layers were dried over MgSO4 and concentrated to give a residue, which was purified by flash chromatography to provide the title compound as a white solid (157 mg, 0.315 mmol, 42%). 1H NMR (400 MHz, CDCl3) delta 1.49 (s, 6H), 3.72 (s, 3H), 3.85 (s, 3H), 4.13 (d, 2H), 4.65 (br, IH), 6.45 (dd, IH), 6.48 (m, 2H), 6.51 (d, IH), 6.60 (m, IH), 6.64 (d, IH), 6.76 (dd, IH), 6.80 (t, 2H), 7.00 (dt, IH), 7.13 (s, IH). MS (EI) m/z 498 [M+H]+.

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; EXELIXIS, INC.; BOLLU, Venkataiah; BOREN, Brant, Clayton; DALGARD, Jackline, Eve; FLATT, Brenton, T.; HAQ, Nadia; HUDSON, Sarah; MOHAN, Raju; MORRISSEY, Michael; PRATT, Benjamin; WANG, Tie-lin; WO2010/93845; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

14752-66-0, These common heterocyclic compound, 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, 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.

In a dry test tube, add 59mg and 198mg benzimidazole of chlorobenzene sulfinateSodium, was added 89mg of NBS. Was then added 2mL of 1,4-dioxane to dissolve the solid, the reaction solution was stirred at 25 12 hours. After completion of the reaction, ethyl acetate and water extraction, the resulting organic phase was concentrated on a rotary evaporator, silica gel column (ethyl acetate and petroleum ether, the volume ratio of 1: 3) to give the product 124mg, yield 85% , the following reaction formula:

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 14752-66-0.

Reference:
Patent; Wenzhou Medical College; Xia, Qinqin; Fu, Lili; Bao, Xiaodong; Liu, Zhiguo; Liang, Guang; (11 pag.)CN105693621; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-29-8, The chemical industry reduces the impact on the environment during synthesis 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, I believe this compound will play a more active role in future production and life.

Step 1 : To a lOOmL three-necked flask was added 20mL toluene and compound 13a (3g, 0.014mol, l .Oeq), compound 13b (4.3g, 0.022mol, 1.5eq) and t-BuONa (2.064g, 0.022mol, 1.5eq). The reaction was heated to 80oC with nitrogen. Then BINAP (0.3g, 0.42mmol, 0.03eq) and Pd2(dba)3.CHCl3 (0.15g, 0.14mmol, O.OOleq) was added to the stirred mixture . The reaction was heated to reflux for 18h. The solution was cooled, concentrated and extracted with 30 EA from lOmL water. The organic layer was washed with brine , dried , concentrated in vacuum and purified by column chromatography on silica gel eluted with PE: EA= 10: 1 to afford the compound 13c (4g, HPLC: 98%) as a white solid. Yield: 86%.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-chloro-2-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; LIANG, Congxin; (62 pag.)WO2018/5713; (2018); 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. 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride, A new synthetic method of this compound is introduced below., 41965-95-1

9-[(3-chloro-4-methoxybenzyl)amino]-2-ethyl-7-(trifluoromethyl)-2,3-dihydro-lH- pyrrolo[3,4-b]quinolin-l-one M [00304] A solution of 49 (0.095 mmol), 3-chloro-4-methoxybenzylamine hydrochloride (0.14 mmol) and (‘pr)2NEt (0.57 mmol) in n-propanol (1.0 mL) was heated to 90 C for lh. The solvent was evaporated off and the residue was purified by flash chromatography (AcOEt) to give the final product M. MS ESI (m/z) 450 (M+H)+; 1H NMR (400 MHz, CDC13) delta 8.58 (t, IH, J=6.0 Hz), 8.46 (s, IH), 8.0 (d, IH, J=8.8 Hz), 7.80 (dd, IH, Ji=2.0, J2=9.2 Hz), 7.45 (d, IH, J=2.0 Hz), 7.32 (dd, IH, Ji=2.4, J2=8.4 Hz), 6.95 (d, IH, J=8.0 Hz), 4.95 (d, 2H, J=6.0 Hz), 4.41 (s, 2H), 3.90 (s, 3H), 3.67 (q, 2H, J=7.2 Hz), 1.3 (t, 3H, J=7.2 Hz)

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; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; LANDRY, Donald, W.; DENG, Shixian; FIORITO, Jole; ARANCIO, Ottavio; WASMUTH, Andrew; WO2015/9930; (2015); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

7781-10-4, 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. 7781-10-4, name is 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Add N-bromosuccinimide (418 g, 2.35 mol) portionwise over 20 min at 15 C to a solution of 4-chloro-7-methyl-pyrrolo[2,3-d]pyrimidine (355 g, 2.12 mol) indichloromethane (3.19 L), and stir at 23 C for 3 h. After this time, filter, wash with H20 (5.32 L), and dry to give the title compound (448 g, 86%) as a white solid. ES/MS m/z (35C1,79Br) 245.9 (M+H).

The synthetic route of 7781-10-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; CIFUENTES-GARCIA, Marta Maria; GARCIA-PAREDES, Maria Cristina; (34 pag.)WO2018/194885; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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,
Chlorides – an overview | ScienceDirect Topics