Category: chlorides-buliding-blocks

Application of 13726-14-2, 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. 13726-14-2, name is 4-Chloro-3-methoxyaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step-1: N-(4-chloro-3-methoxyphenyl)acetamide [0112] To a solution of 4-chloro-3-methoxyaniline (50 g, 317 mmol) and DIPEA (110 mL, 635 mmol) in CH2Cl2 (700 mL) was added acetic anhydride (36 mL, 381 mmol) drop wise at 0 C and the reaction mixture was stirred at room temperature for 3 h. The reaction then was quenched with water (250 mL) and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (100 mL x 3). The combined organic layers were dried (Na2SO4), concentrated and purified by flash chromatography with CH2Cl2/MeOH to give N- (4-chloro-3-methoxy phenyl)acetamide (71 g, quantitative yield) as a white solid.

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, 4-Chloro-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ASHWELL, Susan; CAMPBELL, Ann-Marie; CARAVELLA, Justin Andrew; DIEBOLD, R. Bruce; ERICSSON, Anna; GUSTAFSON, Gary; LANCIA, David R.; LIN, Jian; LU, Wei; WANG, Zhongguo; (147 pag.)WO2016/171755; (2016); 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. 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene

Accurately weigh 65.12g (0.2Mol) of raw material A, then add toluene / tetrahydrofuran mixture (V toluene / tetrahydrofuran = 2:1), dilute to 500ml, mix and pump into the microreactor at a flow rate of 14ml / min a reaction unit,At the same time, the concentration of 2.0mol / L n-butyl lithium solution was pumped into the first reaction unit at a flow rate of 3.4ml / min for thorough mixing to produce lithium halide exchange reaction, the residence time was 27 seconds, and the reaction temperature was controlled at -15 C. After the reaction solution flows out of the first reaction unit,At the same time, the raw material C was flowed into the second reaction unit of the microreactor at a flow rate of 2.2 ml/min to carry out a lactone condensation reaction.The residence time of the reaction in this step was 22 seconds, and the reaction temperature of the second reaction unit was controlled to be -15 C. Accurately prepare a mixture of 300 ml of methanol and methanesulfonic acid (V methanol / methanesulfonic acid = 4:1),It is pumped into the third reaction unit of the microreactor at a flow rate of 3.5 ml/min, and mixed with the reaction liquid flowing out from the second reaction unit.The residence time of the reaction in this step is 19 seconds, and the reaction temperature controlled by the reaction unit is 5 C. After the reaction liquid flows out from the third reaction unit,At the same time, the prepared mixture of boron trifluoride diethyl ether and triethylsilane was pumped into the fourth reaction unit at a flow rate of 3.5 ml/min.The residence time of the reaction unit is 15 seconds, the temperature of the fourth reaction unit is controlled to be 5 C, and the liquid discharged from the fourth reaction unit is continuously collected 100 ml.Finally, it was added to 200 ml of n-heptane, stirred and crystallized, and kept at 0 C for 1 hour, and filtered to obtain a crude product of dapagliflozin.

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; Shandong Heroic Chemical Co., Ltd.; Ning Jiabin; Ren Miaomiao; Ge Yuan; Wang Wei; Sheng Zhen; Zheng Hao; (12 pag.)CN109400561; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 104-52-9, name is 3-Phenylpropyl Chloride, 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. Application In Synthesis of 3-Phenylpropyl Chloride

(1) 1-Bromo-3-chloro-1-phenylpropane 3-Chloro-1-phenylpropane (3.09 g, 20 mmol.), N-bromosuccinimide (3.56 g, 20 mmol.), benzoyl peroxide (catalytic amount), and carbon tetrachloride (30 mL) were mixed, and the resulting mixture was heated to reflux for 15 min while it was exposed to a light of 100V/100 W, to perform a reaction. Insolubles were filtered off. The reaction liquid was washed with an aqueous saturated sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and placed under reduced pressure to distill the solvent off, to give 4.58 g of the desired compound (yield 98%) as an oil. 1 H-NMR (CDCl3) delta: 2.1-2.9 (2H, m), 3.3-3.9 (2H, m), 5.16 (1H, dd, J=7 Hz, 10 Hz), 7.1-7.5 (5H, m).

The synthetic route of 3-Phenylpropyl Chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; US5773437; (1998); A;,
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. 97329-43-6, name is 1-Bromo-2-chloro-3-methylbenzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-2-chloro-3-methylbenzene

A mixture of 1-bromo-2-chloro-3-methylbenzene (4.0 g, 19.6 mmol), Pd2dba3 (1014 mg, 0.98 mmol), Xantphos (566 mg, 0.98 mmol), tert-butyl carbamate (3.41 g, 29.4 mmol) and Cs2CO3 (9.58 g, 29.4 mmol) in dioxane (120 mL) was stirred at 110 C. for 2 h and then cooled to rt. Water (150 mL) was added and the mixture was extracted by EtOAc (150 mL×2). The organic layer was dried and concentrated. The residue was purified by flash column chromatography (PE , 100%) to afford the title compound (4.2 g, 89%). MS (ES+)C12H16ClNO2 requires: 241, found: 187 [M-55+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; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; JONES, Philip; CZAKO, Barbara; CARROLL, Christopher L.; MANDAL, Pijus; CROSS, Jason; (64 pag.)US2020/48249; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6H3ClF2O2S

To a solution of 3,5-difluorobenzenesulfonyl chloride (25 g, 0.117 mol) in THF (150 rnL) was added 35% aq. NH4OH (120 rnL) over 1 h in an ice-bath. After the reaction was complete, it was evaporated in vacuo. To a solution of this residue in water (150 mL) was added 2N HCl (1 mL). After stirring 1 h, the reaction mixture was filtered and dried under high vacuum to give 3,5-difluorobenzenesulfonamide as a light brown solid (19.9 g, 88%). 1H NMR (400MHz, CDCl3) delta 7.49-7.44 (m, 2H), 7.04-6.99 (m, 2H).

The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 63624-28-2, These common heterocyclic compound, 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, 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: A mixture of ethyl 6-amino-9-ethyl-1-methyl–carboline-3-carboxylate 11a (1.0 mmol) and 3,4-dimethoxybenzene sulfonylchloride (1.0 mmol) in DMF (5 mL) was stirred for 5min at room temperature, followed by the addition of pyridine(4.0 mmol) was added. The mixture was stirred for an additional0.5 h. After adding ice water (10 mL), the mixture wasextracted with EtOAc (320 mL). The organic phase waswashed with brine (220 mL), dried over anhydrous Na2SO4,and concentrated in vacuum. The residue was purified oversilica column chromatography using petroleum ether (PE) :EtOAc (1:1, v/v) as eluent to afford the title compound 12a.

Statistics shows that 2,4-Dimethoxybenzene-1-sulfonyl chloride is playing an increasingly important role. we look forward to future research findings about 63624-28-2.

Reference:
Article; Chen, Jing; Du, Wenting; Tao, Xuefen; Huang, Jiawei; Song, Yuliang; Ying, Huazhou; Letters in drug design and discovery; vol. 10; 9; (2013); p. 879 – 885;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1303587-99-6, 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. 1303587-99-6, name is 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis ofN-(3-methoxy-4-(2-methylpyridin-4-yl) phenyl)-, 8-dihydro-6H-pyrimido [5, 4- b] [I, 4] oxazin-2-amine [0350] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (1 g, 5.81 mmol) in isopropyl alcohol (20 mL) under argon atmosphere were added 3- methoxy-4-(2-methylpyridin-4-yl) aniline (1.2 g, 5.81 mmol) and concentrated hydrochloric acid (12M, 0.5 mL) at RT. The reaction mixture was stirred at 120 C for 48 h in a sealed tube. After completion of the reaction (monitored by TLC), the volatile components were removed in vacuo. The resultant residue was basified with a saturated sodium bicarbonate solution (50 mL) and extracted with a 10% MeOH:CH2Cl2 solution (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography using 6% MeOH:CH2Cl2 to afford N-(3-methoxy-4-(2-methylpyridin-4-yl) phenyl)-7, 8-dihydro-6H- pyrimido [5, 4-b] [1, 4] oxazin-2-amine (950 mg, 47%) as a pale yellow solid. 1H-NMR (DMSO-d6, 500 MHz): delta 8.96 (s, IH), 8.36-8.35 (m, IH), 7.73 (s, IH), 7.51 (s, IH), 7.37 (d, 2H), 7.33 (s, IH), 7.29-7.28 (m, IH), 7.21 (d, IH), 4.07-4.05 (m, 2H), 3.78 (s, 3H), 3.45-3.43 (m, 2H), 2.47 (s, 3H); LC-MS: 350.2 (M+1); (column; X-Bridge C-18 (50 3.0 mm, 3.5 mupiiota); RT 2.47 min. 0.05% aq TFA: ACN; 0.80 mL/min); UPLC (column; Acquity UPLC BEH C-18 2.1 X 50 mm, 1.7 mupiiota); RT 1.20 min. ACN: 0.025% TFA (Aq); 0.50 mL/min; TLC: 10% MeOH:CH2Cl2 (R/. 0.6).

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-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); 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. 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, A new synthetic method of this compound is introduced below., Safety of 3-Chloro-2-chloromethyl-1-propene

Example 3 12,13-(2-methylene-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole (Compound 22) 12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole (Compound 23) 9-hydroxymethyl-12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole (Compound 212) Compound 1c (1.56 g, 5.0 mmol, 1.0 equiv) was added to Cs2CO3 (4.89 g, 15.0 mmol, 3.0 equiv) in DMF (20 mL) under N2 at room temperature. The mixture was stirred for 5 min, then 3-chloro-2-chloromethyl-prop-1-ene (625 mg, 5.0 mmol, 1.0 equiv) was added. The mixture was stirred at rt for 24 hours and poured into H2O (200 mL). The resulting yellow solid was filtered and washed with H2O (50 mL×2) and Et2O/hexane (1:1, 50 mL×3), then dried in vacuo to provide Compound 22 (1.46 g, 80%) as a yellow solid. 1H NMR: (d6-DMSO) delta 4.96 (s, 2H), 5.28 (s, 2H), 5.30 (s, 2H), 5.80 (s, 2H), 7.28 (t, 1H, J=8.1 Hz), 7.37 (t, 1H, J=7.2 Hz), 7.52 (t, 1H, J=8.1 Hz), 7.57 (t, 1H, J=8.1 Hz), 7.81 (d, 1H, J=8.1 Hz), 7.87 (d, 1H, J=7.8 Hz), 8.07 (d, 1H, J=7.2 Hz), 8.53 (s, 1H), 9.31 (d, 1H, J=7.8 Hz). MS m/z 386 (M+Na), 364 (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; Wilson, Lawrence J.; Murray, William V.; Yang, Shyh-Ming; Yang, Cangming; Wang, Bingbing; US2007/249590; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 104-52-9,Some common heterocyclic compound, 104-52-9, name is 3-Phenylpropyl Chloride, molecular formula is C9H11Cl, 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.

Aluminum chloride (160 g, 1.2 mol, 2 q) was added to a 500 ml three-necked flask to keep the reaction solution at a temperature of not higher than -15 C. Pre-mixed 3-chlorophenyl propane (93 g, 0.6 mol, lq) and n-octanoyl chloride (116 g, 0.72 mol, 1.2 eq). After completion of the dropwise addition, the reaction was complete at -5 C until the reaction was complete [reaction takes about 8 to 14 hours, HPLC detection: 3-chlorophenylpropane The mixture was slowly poured into 1200 ml of 5% hydrochloric acid and extracted with ethyl acetate (200 ml x 3 times). The organic layers were combined and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate (50 g) was dried and filtered, and the filtrate was concentrated at about no more than 40 C to give a yellow oil to octanoylchloropropylbenzene (152 g, HPLC purity 95.86% yield 90%).

The synthetic route of 104-52-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHENGDU HONGDA PHARMACEUTICAL CO., LTD.; KE, XIAO; CHANG, HEXI; YE, YONG; (13 pag.)CN103804123; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, 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 14752-66-0, Application In Synthesis of Sodium 4-chlorobenzenesulfinate

General procedure: To a solution of N-methylindoles (1.0mmol), sodium aryl sulfonates (0.5mmol), catalyst I2 (0.75mmol) and tert-Butyl hydroperoxide (1.5mmol) in methanol (2mL) were added. The reaction mixture was stirred at 80C for 12h. Then the reaction mixture was cooled to room temperature, diluted with brine (15mL) and extracted with EtOAc (3×25mL). The organic layer dried over anhydrous MgSO4 and concentrated in vacuo. The residue was further purified by column chromatography on silica gel (Petroleum ether/EtOAc=5:1) to afford the compounds 6a, 7a-b, 8a-h, 9a-k, 10a-d with yield of 9%-95%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Sodium 4-chlorobenzenesulfinate, and friends who are interested can also refer to it.

Reference:
Article; Xia, Qinqin; Bao, Xiaodong; Sun, Chuchu; Wu, Di; Rong, Xiaona; Liu, Zhiguo; Gu, Yugui; Zhou, Jianmin; Liang, Guang; European Journal of Medicinal Chemistry; vol. 160; (2018); p. 120 – 132;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics