Category: chlorides-buliding-blocks

Reference of 468075-00-5,Some common heterocyclic compound, 468075-00-5, name is 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, molecular formula is C7H3BrClF3O, 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.

(a) 2-Chloro-5-trifluoromethoxy-benzoic acid methyl ester A mixture of 2-bromo-1-chloro-4-trifluoromethoxy-benzene (5 g, 18.2 mmol), triethylamine (5.51 g, 54.5 mmol), and Pd(dppf)Cl2 (1.33 g, 1.82 mmol) in methanol (200 mL) was stirred at 80 C. under carbon monoxide (50 Psi) overnight, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography (5% EtOAc in petroleum ether) to give the title intermediate as a colorless liquid (3.4 g, 74% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, its application will become more common.

Reference:
Patent; LONG, Daniel D.; MCKINNELL, Robert Murray; JIANG, Lan; LOO, Mandy; LEPACK, Kassandra; VAN ORDEN, Lori Jean; OGAWA, Gavin; HUANG, Xiaojun; ZHANG, Weijiang; US2013/115194; (2013); A1;,
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Reference of 13526-66-4,Some common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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.

13.9 g (59.8 mmol) 3-bromo-6-chloro-imidazo[1 ,2-b]pyridazine were suspended in 508 mL 1 ,4-dioxane. 10.1 g (62.8 mmol) 2-benzofuranylboronic acid, 2.76 g (2.29 mmol) tetrakis(tn’phenylphosphino)palladium-(0) and 19.0 g (179 mmol) sodium carbonate were added. The obtained mixture was heated to 100C for 24 h. 400 mL of a saturated aqueous ammonium chloride solution were added. The obtained mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the obtained solid material was digested in 40 mL of a mixture of dichloromethane and methanol (8:2), filtered off and dried in vacuo to yield 5.42 g (44%) of the title compound as solid material. 1H-NMR (300MHz, DMSO-d6): delta [ppm]= 7.23 – 7.40 (2H), 7.51 (1 H), 7.59 – 7.67 (2H), 7.77 (1 H), 8.33 – 8.40 (2H). LCMS (Method 1 ): Rt = 1.35 min; MS (ESIpos) m/z = 270 [M+H]+.

The synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Intellectual Property GmbH; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHOLZ, Arne; LIENAU, Philip; GNOTH, Mark, Jean; BOeMER, Ulf; GUeNTHER, Judith; HITCHCOCK, Marion; WO2013/34570; (2013); A1;,
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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 870-24-6 as follows. Quality Control of 2-Chloroethanamine hydrochloride

beta- chloroethylamine hydrochloride 30g (0.26mol), phosphorusoxychloride 40g (0.26mol) were added in 200mL of dichloromethane and cooled to-20 deg.C. Under stirring, add dropwise triethylamine 26g (0.26mol) the methylenechloride solution 100mL. After the addition is complete, the reaction wasgradually raised to room temperature and reacted overnight. the solvent wasdistilled off under reduced pressure to reduced pressure distillation beta-chloroethylaminophosporylchloride 33.6 g, 53.6% yield.

According to the analysis of related databases, 870-24-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Institute of Technology; Wen, Hongliang; Shen, Xiurui; Huang, Cipan; Wang, Xiaodi; (47 pag.)CN105294756; (2016); A;,
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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. 7149-75-9, name is 4-Chloro-3-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Chloro-3-methylaniline

Step 2 (0404) To a mixture of 1-(3-formylbenzyl)azetidine-3-carboxylic acid methyl ester (330 mg), 4-chloro-3-methylphenylamine (243 mg) and methanol (8 mL) was added decaborane (90 mg), and the mixture was stirred at room temperature for 2 hours. After the mixture was diluted with ethyl acetate, to the resulting mixture was added aminopropyl silica gel powder (3 g). The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by aminopropyl silica gel column chromatography (eluent: 20percent-50percent ethyl acetate/hexane, gradient elution) to give the title compound (450 mg). The structural formula was illustrated in Table 1. [table-us-00001-en] Reference Example Structural formula 1-1 (0405) The physical data of Reference Example 1-1 was shown below. Reference Example 1-1 (0406) MS (ESI, m/z): 359(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 7149-75-9.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Inoue, Hitoshi; Ohno, Kohsuke; Nakamura, Tetsuya; Ohsawa, Yusuke; (58 pag.)US2016/362368; (2016); A1;,
Chloride – Wikipedia,
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These common heterocyclic compound, 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, 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. Recommanded Product: 2-Chloro-N,N-dimethylethanamine hydrochloride

The title compound was obtained as a colorless oil in 49 % yield by following the general procedure B. UV (EtOH) mm: 219 and 276 nm. IR (nujol): 2945, 2822, 2727, 1685, 1597, 1510, 1466, 131 1,1258, 1216 1 160, 1030 and 834 cm ‘. NMR (300 MHz, CDCI3): delta 2.37 (6H, s, 2 x NC¾), 2.81(2H, t, J = 5.1Hz, -NCH2), 4. 1 1 (2H, t, J = 5.4 Hz, OCH2), 6.99 (2H, d, J = 8.1 Hz, 2 x Ar-H), 7.81 (2H, d, J = 7.8 Hz, 2 x Ar-H), 9.85 (1H, s, CHO). 13C NMR (75.5 MHz, CDC13): delta 45.68 (2 x NC¾), 57.90 (NCH2), 66.08 (OCH2), 1 14.82 (C-2 & C-6), 130.04(C-1), 13 1.92 (C-3 & C-5), 163.72 (C-4), 190.75 (C=0). HRMS m/z calculated for C?H,5N02 [M+H]+ 194.1 176, observed [M+Hf 194. 1 168. In a dried single-neck round bottom flask, 4-hydroxylbenzaldehyde (40 mmol), potassium carbonate (122 mmol) and dry acetone (160 ml) were taken and the contents refluxed for 2 h. The reaction mixture was brought to room temperature and catalytic amount of potassium iodide was added, followed by the gradual addition of the appropriate dialkylaminoethyl chloride hydrochloride (45 mmol) dissolved in dry acetone (50 ml) through a pressure-equalizing addition funnel and the reaction mixture was allowed to reflux again. The contents were regularly monitored for reaction progress by TLC using 10 % methanol/dichloromethane as the solvent system. The reaction was generally complete in 10-13 h. At this point, reaction mixture was filtered under suction and the solid inorganic salts were washed with acetone (3 x 60 ml). The solvent was evaporated under reduced pressure and the residue was purified by column chromatography over silica gel (6-8 % methanol in dichloromethane, v/v as eluent) to afford the six pure 4-dialkylaminoethoxybenzaldehydes as colorless oils in 49-92 % yields. The structures of these products were unambiguously established from the analysis of their spectral data (IR, NMR, l3C NMR and mass spectra).

The synthetic route of 2-Chloro-N,N-dimethylethanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DALHOUSIE UNIVERSITY; JHA, Amitabh; WO2012/79154; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 7149-75-9, name is 4-Chloro-3-methylaniline, molecular formula is C7H8ClN, 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. category: chlorides-buliding-blocks

Step 1 (0424) To a mixture of 5-hydroxy-3,4-dihydro-2H-naphthalen-1-one (693 mg), 4-chloro-3-methylphenylamine (550 mg) and methanol (20 mL) was added decaborane (236 mg), and the mixture was stirred at room temperature for 8 hours. After the mixture was diluted with ethyl acetate, to the resulting mixture was added aminopropyl silica gel powder (5 g). The resulting mixture was filtered and the filtrate was concentrated under reduced pressure to give 5-(4-chloro-3-methylphenylamino)-5,6,7,8-tetrahydronaphthalen-1-ol (1.1 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7149-75-9, its application will become more common.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Inoue, Hitoshi; Ohno, Kohsuke; Nakamura, Tetsuya; Ohsawa, Yusuke; (58 pag.)US2016/362368; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature 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.

[[002511] To a mixture of 6-chloro-4- (3, 3-dimethyl-piperidin- 4-ylamino) -chromen-2-one, di-HBr salt (88 mg, 0.188 mmol) in THF was added Cs2CO3 (287 mg, 0.881 mmol) and the suspension was stirred for 5 min under nitrogen before 5-chloromethyl- benzo [[1,] 3] dioxole (124 mg, 0.363 mmol) was added dropwise. The mixture was stirred for 70 h at [25 C] before being refluxed 24 h. The reaction was concentrated with nitrogen flow. The crude product was partitioned between saturated aqueous [NAHC03] and EtOAc and the aqueous layer was extracted with EtOAc [(3X).] The combined organic layers were washed with saturated aqueous [NACL,] dried over [MGS04,] filtered, concentrated, and purified by C-18 RP LC-MS chromatography to afford 33 mg [(40%)] of the title compound as a white solid. MS (ESI (+) [Q1MS)] m/z 442 [(M+H)] + ; 1H NMR (300 MHz, DMSO) [B] ppm 0. [80] (s, 3H), 1. [06] (s, 3H), 1.52-1. 62 (m, [1H),] 1.84-2. 14 (m, 3H), 2.37-2. 55 (m, 1H), 2.80-2. 90 (m, 1H), 3.25-3. 37 (m, 1H), 3.39-3. 52 (m, 2H), 5.44 (s, 1H), 5.97-6. 02 (m, 2H), 6.73-6. 90 (m, 4H), 7.31-7. 38 (m, 1H), 7.60-7. 67 (m, 1H), 8.45-8. 50 (m, 1H).

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:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2003/106452; (2003); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2106-02-7, These common heterocyclic compound, 2106-02-7, name is 2-Chloro-4-fluoroaniline, 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.

Example 8; Synthesis of N-(2-chloro-4-fluoropheny?-N-(2-cvano-4-fluorophenv?-2-(5- isoquinolinyloxy)acetamide; 1 ) 2-[Y2-chloro-4-f*luorophenyl)amino1-5-fluorobenzonitrile; To a solution of 2-chloro-4-fluoroaniline (3.07 g) in N-methyl-2-pyrrolidone (40ml) was added potassium t-butoxide (4.97 g), the solution was stirred for 10 minutes, added 2,5-difluorobenzonitrile (3.26 g) in N-methyl-2-pyrrolidone (4ml), and then the solution was stirred for 4 hours at room temperature. While cooling on ice, water was added and then extraction was conducted with ethyl acetate. The organic phase was washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resultant residue was purified by a silica gel chromatography (hexane:chloroform=6: l to 1 : 1) to obtain an orange solid, which was washed with hexane (40 ml) to obtain the title compound (2.62 g) as a pale orange solid.

The synthetic route of 2106-02-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BANYU PHARMACEUTICAL CO.,LTD.; SUGIMOTO, Yuichi; SATOH, Atsushi; NISHIMURA, Teruyuki; WO2010/117084; (2010); A1;,
Chloride – Wikipedia,
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Electric Literature of 13918-92-8, The chemical industry reduces the impact on the environment during synthesis 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, I believe this compound will play a more active role in future production and life.

To the solution of 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (400 mg, 1.6 mmol) in pyridine (5 mL) was added 2,4-difluorobenzenesulfonyl chloride (407 mg, 1.9 mmol) slowly, the reaction mixture was stirred at room temperature overnight, the solvent was evaporated in vacuo, and the residue was treated with brine (5 mL) and extracted with EtOAc (3×10 mL). The combined organic layer was evaporated in vacuo, and the residue was purified by column chromatography using petroleum ether_EtOAc=5:1 as eluent to afford the desired product 2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide as white solid in 59% yield (400 mg). m/z 427 (M+H)+.

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, 2,4-Difluorobenzene-1-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Su, Weiguo; Zhang, Weihan; Yang, Haibin; US2013/190307; (2013); A1;,
Chloride – Wikipedia,
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Some common heterocyclic compound, 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, molecular formula is C3H9Cl2N, 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. Computed Properties of C3H9Cl2N

General procedure: Toa suspension of lawsone (0.87 g, 5.0 mmol) in ethanol(10 mL) were added sequentially: i) the corresponding amine (5.5 mmol) – andtriethylamine (5.0 mmol, 0.7 mL) in the case of 3-(chloropropyl)aminehydrochloride – and ii) the respective aldehyde (6.0 mmol). The reactionmixture was stirred at RT, in the dark for 12h, after which time the orangeprecipitate was filtered, washed with ethanol, diethyl ether and dried undervacuum.Forthe syntheses of 6a, 6b, 6e, 6f, 6g and 6h, which are more soluble than the other products, the reactionswere carried out in the same amount of ethanol, but using 10.0 mmol of lawsone,10.0 mmol of heptylamine and 12.0 mmol of aldehydes.Compounds4a, 5a, 8a, 4b, 5b, 4c, 5c, 4d, 5d, 6d, 7d, 8d, 9e, 5g, 4h and 5h were synthesized as describedpreviously.3-5

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6276-54-6, its application will become more common.

Reference:
Article; da Silva, Gustavo B.; Neves, Amanda P.; Vargas, Maria D.; Marinho-Filho, Jose D.B.; Costa-Lotufo, Leticia V.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3537 – 3542;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics