Tag: M.W=100-200

Electric Literature of 2533-69-9, 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 2533-69-9 as follows.

2.00 g (12.0 mmol) Methyl-3,4-diamino-benzoate were dissolved in 50 ml concentrated acetic acid. Then 2.09 ml (1.4 equiv.) methyl-2,2,2-trichloroacetimidate were added slowly and the resulting mixture was stirred at room temperature for 2 h. The mixture was diluted with 100 ml toluene and the solvent was removed under reduced pressure. The residue was taken up in dichloromethane and washed once with a saturated NaHCO3-solution and once with brine. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure to give pure methyl-2-trichloromethyl-1H-benzoimidazole-5-carboxylate as a light brown amorphous solid. Yield: 3.64 g MS (ES+): m/e = 293, chloro pattern.

According to the analysis of related databases, 2533-69-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aventis Pharma Deutschland GmbH; EP1479676; (2004); A1;,
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Reference of 14752-66-0,Some common heterocyclic compound, 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, molecular formula is C6H4ClNaO2S, 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: I2 (0.5 mmol) was added to a solution of alkynes (0.5 mmol),sodium benzenesulfnates (1.0 mmol) and DTBP (1.0 mmol)in C2H5OH: H2O (2 mL:2 mL), and the reaction mixture wasstirred and heated at 60C for 2.0 h. Then, the mixture wascooled to room temperature, quenched by Na2S2O3, dilutedwithwaterandextractedbyCH2Cl2 (10mL ×3).Thecombined organic layer was washed with water and dried over anhydrousNa2SO4. The solvent was removed in vacuum and the targetcompound was obtained by column chromatography on silicagel (petroleum ether: ethyl acetate = 15: 1, v: v).

The synthetic route of 14752-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bi, Wenzhu; Ren, Chunyan; Jia, Linguo; Xia, Xiaoyi; Chen, Xi; Chen, Xiaolan; Zhao, Yufen; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 192; 4; (2017); p. 391 – 396;,
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Application of 39226-95-4, A common heterocyclic compound, 39226-95-4, name is 2,3-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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: Under nitrogen atmosphere, a Schlenk tube was sequentially charged with cyclicdiaryliodonium salt (1.0 equiv), copper catalyst A1 or A2 (5.0 mol%), Na2CO3 (3.0 equiv) anddichloromethane (0.05 M). After the mixture was chilled to proper temperature, the appropriateamine (1.2 equiv) was added and stirred for the time indicated in the experimental procedures.The reaction mixture was filtered through a plug of celite with ethyl acetate. The filtrate wasconcentrated under reduced pressure, and the residue was purified by column chromatographyon silica gel to deliver the corresponding product.

The synthetic route of 39226-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Kun; Duan, Longhui; Xu, Shibo; Jiang, Julong; Fu, Yao; Gu, Zhenhua; Chem; vol. 4; 3; (2018); p. 599 – 612;,
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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. 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, This compound has unique chemical properties. The synthetic route is as follows., name: 5-(Chloromethyl)benzo[d][1,3]dioxole

Preparation of 1, 3-benzodioxol-5-ylmethyl isopropyl sulfone 7.8 g of 5-(chloromethyl)-1, 3-benzodioxol was dissolved in 20 ml of anhydrous tetrahydrofuran and 20 ml of diethyl ether and then added to magnesium at 0C, and reacted for 10 minutes. The reactant was heated to 50C and reacted for 1 hour. The reaction mixture was cooled to 0C and then slowly added to a flask containing [1, 3-bis (diphenylphosphino) propane] nickel (II) dichloride as a catalyst. After the addition of 3. 9 ml isopropane sulfonyl chloride, the mixture was reacted for 30 minutes and the reactant was heated to 50C and reacted for 1 hour. Then, its pH was adjusted to 7 with dilute hydrochloric acid. The resulting mixture was extracted with diethyl ether and distilled water, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was fractionated by column chromatography using ethyl acetate: n-hexane (1: 3), to give 0.6 g of the title compound of the following formula ld (Rf : 0.35, Yield: 5%). [Chemical Formula 1d] The compound was dissolved in CDC13 and TMS and then characterized by IH NMR spectroscopy. The result is as follows ; ‘H NMR 8 : 1.60-1. 62 (d, 6H, J=6.7Hz), 2.79 (s, 2H), 3.75-3. 78 (m, 1H), 5.91 (s, 2H), 6.66 (m, 3H)

According to the analysis of related databases, 20850-43-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HAN, Sang Min; LEE, Myung Hee; CHOI, Won Chul; WO2005/70915; (2005); A1;,
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Application of 918538-05-3, 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

j00535j Compound rac**A2 (50 mg, 0.3 mmol) and 2,4-dichloropyrrolo[2,1-JI[1,2,4jtriazine (52 mg, 0.3 mmol) were dissolved in 2-propanol (1 mL). After stirring at room temperature for 3 hours, N,N-diisopropylethylamine (80 .iL, 0.5 mmol) was added, and the reaction mixture was stirred for 16 hours, concentrated onto silica and purified by column chromatography [chloroform: 7M NH3 in methanol = 1:0 to 9:11 to afford compound rac-6-int (59 mg, 64% yield). LCMS (1): tR=2.498 mi, (ES) m/z (M+H) = 333.0.

The synthetic route of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
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Application of 1871-57-4,Some common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, molecular formula is C4H6Cl2, 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 suspension of sodium hydride (purity> 55%, 11.4 g) in N, N-dimethylformamide (150 mL),Under ice cooling, add 3-chloro-2-chloromethyl-1-propene (12.7 mL, CAS number: 1871-57-4),After stirring for 10 minutes at the same temperature,2- (tert-Butoxycarbonylamino) -1-ethanolA solution of (19.3 g, CAS number: 26690-80-2) in tetrahydrofuran (150 mL) was added dropwise over one and a half hours, and the mixture was stirred at room temperature for two and a half hours.The reaction solution was ice-cooled, water was added, and the mixture was extracted 3 times with diethyl ether,The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate.After filtration and concentration under reduced pressure, the obtained residue is purified by silica gel column chromatography (n-hexane / ethyl acetate) to give the title compound.(16.0 g) was obtained as an oil.

The synthetic route of 1871-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Healthcare Co Ltd; Naito, Hiroyuki; Suzuki, Takayuki; Murata, Takeshi; Kawai, Junya; Higuchi, Saito; (99 pag.)JP2020/45306; (2020); A;,
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Synthetic Route of 367-22-6, 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. 367-22-6, name is 4-Chloro-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

4.1.1 Ethyl 2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetate (6a) To a stirred solution of 3-fluoroaniline (1.11 g, 10.0 mmol) in CHCl3 (30.0 mL) was added dropwise N-chlorosuccinimide (NCS) in CHCl3 (20.0 mL) at 0 C. The mixture was stirred at 0 C for 42 h. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in Et2O. The mixture was washed with water, and dried over MgSO4. Concentration under reduced pressure followed by flash chromatography over silica gel with EtOAc/n-hexane gave 4-chloro-3-fluoroaniline (259.4 g, 18% yield) as crystalline solids. To a stirred solution of the above aniline (259.4 mg, 1.78 mmol) in THF (8.9 mL) were added at 0 C ethyl chloroglyoxylate (237.3 muL, 2.14 mmol) and Et3N (296.6 muL, 2.14 mmol). The mixture was stirred at room temperature for 12 h. After the precipitate was filtrated off, the filtrate solution was concentrated under reduced pressure. The residue was dissolved in EtOAc, and washed with 1.0 M HCl, saturated NaHCO3 and brine, then dried over MgSO4. Concentration under reduced pressure to provide the title compound 6a (435.2 mg, 99% yield) as brown crystals, which was used without further purification. 1H NMR (500 MHz, CDCl3) delta 1.44 (t, J = 7.50 Hz, 3H), 4.43 (q, J = 7.50 Hz, 2H), 7.24-7.25 (m, 1H), 7.35-7.40 (m, 1H), 7.70-7.75 (m, 1H), 8.93 (br, 1H); 13C NMR (125 MHz, CDCl3) delta 13.0, 64.1, 108.5 (d, J = 26.3 Hz), 115.9 (d, J = 3.75 Hz), 117.3 (d, J = 18.8 Hz), 130.9 (d, J = 10.0 Hz), 135.9, 153.9, 158.1 (d, J = 246.3 Hz), 160.5; HRMS (ESI), m/z calcd for C10H10ClFNO3 (MH-) 244.0182, found 244.0183.

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-3-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Narumi, Tetsuo; Arai, Hiroshi; Yoshimura, Kazuhisa; Harada, Shigeyoshi; Hirota, Yuki; Ohashi, Nami; Hashimoto, Chie; Nomura, Wataru; Matsushita, Shuzo; Tamamura, Hirokazu; Bioorganic and Medicinal Chemistry; vol. 21; 9; (2013); p. 2518 – 2526;,
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Related Products of 2533-69-9,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.

To a solution of 3-bromo-4-chlorobenzene-1,2-diamine (4 g, 18 mmol) in AcOH ( 30 mL) was added methyl 2,2,2-trichloroacetimidate (3.5 g, 20 mmol) drop wise at 0 C. Then the reaction mixture was stirred at room temperature overnight. The mixture was poured into water (200 mL), and precipitate was collected and dried to give 4-bromo-5-chloro-2-(trichloromethyl)-1H-benzo[djimidazole (5.5 g, 80%) as a white solid. HPLC/UV purity: 95%; LC-MS (ESI): 349.1 (M + 1).

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

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; PINKERTON, Anthony B.; ARDECKY, Robert J.; ZOU, Jiwen; (256 pag.)WO2018/204176; (2018); A1;,
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Reference of 29882-07-3, These common heterocyclic compound, 29882-07-3, name is 4-Chloro-1,1-dimethoxybutane, 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.

2. 2-(5-Cyanomethyl-1H-indol-3-yl)ethylamine. Hydrochloride 4-Chlorobutanal dimethylacetal (37.07 g, 0.24 mol) was added to a stirred solution of 4-hydrazinobenzyl cyanide hydrochloride (47.0 g, 0.26 mol) in EtOH/H2 O (5:1; 21) and refluxed for 4.5 h. The reaction mixture was evaporated to dryness under vacuum, MeOH (150 ml) added, and the mixture left at 0° C. for 10 h. The resultant pale yellow precipitate was filtered under vacuum, washed with Et2 O/MeOH (5:1; 2*100 ml) and dried. The product was used without further purification (24.1 g, 40percent), m.p. 239°-241° C.; Rf 0.4 in CH2 Cl2 /EtOH/NH3 (40:8:1); 1 H NMR (360 MHz, D2 O) 3.18 (2H, t, J=7.1 Hz, CH2); 3.36 (2H, t, J=7.1 Hz, CH2); 4.02 (2H, s, CH2); 7.22 (1H, dd, J=1.5and 8.4 Hz, Ar-H); 7.36 (1H, s, Ar-H); 7.56 (1H, d, J=8.4 Hz, Ar-H); 7.66 (1H, s, Ar-H).

Statistics shows that 4-Chloro-1,1-dimethoxybutane is playing an increasingly important role. we look forward to future research findings about 29882-07-3.

Reference:
Patent; Merck Sharp & Dohme Limited; US5298520; (1994); A;,
Chloride – Wikipedia,
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4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, 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. COA of Formula: C5H10ClO3P

In a reflux condenser, thermometer, stirrer,Constant pressure dropping funnel 2000mL four-necked flask was added 74g of cyclic phosphorus oxychloride,8 g of anhydrous aluminum trichloride and 800 mL of toluene were added to dissolve them with stirring.Under stirring at 10 C,22.8gBetween cyclohexane diamine four-necked flask,After the addition of cyclohexane diamine is completed,The temperature was raised to 80 C,And the reaction at this temperature 6h, after the reaction was recovered by vacuum distillation solvent,The residue was washed three times with deionized water to give a white solid powder,After drying at 60 C for 10 h, 73.3 g of a product was obtained in a yield of 89.8% by weight.

The synthetic route of 4090-55-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sinopec Corporation; Sinopec Corporation Fushun Petrochemical Institute; Zhao Wei; Wang Xiaolin; Li Ming; Liu Mingrui; Xue Qian; (8 pag.)CN104558039; (2017); B;,
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