Chlorides-buliding-blocks

29671-92-9,Some common heterocyclic compound, 29671-92-9, name is Carbamimidic chloride hydrochloride, molecular formula is CH4Cl2N2, 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 solution of 6-chloro-3-nitropicolinonitrile (25) (0.60 g, 2.7 mmol) and an appropriate aniline was heated at 130 C in isopropanol. After 3-16 h, the solution was concentrated under reduced pressure. The precipitate obtained was neutralized with solution of ammonia in methanol to afford 26-38 as a crude product. The next step was carried out without any purification. To a suspension of 26-38 in methanol (20 mL) and concentrated hydrochloric acid (36%, 2 – 4.0 mL) was added iron powder. The mixture was refluxed until all the starting material had reacted (monitored on TLC). The hot reaction mixture was poured into water (20 mL) and stirred for 5 min. The unreacted iron was removed using a stirring bar retriever, and the aqueous solution was neutralized with ammonium hydroxide to pH 4. The solution was then extracted with chloroform (3 ¡Á 20 mL), and the combined organic layer was washed with water (2 ¡Á 5.0 mL), sodium bicarbonate solution (5.0 mL), and brine (5.0 mL) and dried over anhydrous sodium sulfate. The product (39-52) was obtained as a gummy brown semi-solid. The next step was carried out without any purification and characterization. Mixture of 39-52, chloroformamidine hydrochloride (1 g), and dimethyl sulfone (4.0 g) was heated in an oil bath at 140 C under nitrogen for 15 min. The oil bath was removed, and water (10 mL) was added slowly to the hot reaction mixture. The aqueous solution was cooled to room temperature and extracted with chloroform (3 ¡Á 5 mL) to remove dimethyl sulfone. The aqueous phase was made basic to pH 10 with ammonium hydroxide, followed by removal of water under reduced pressure. The residue was dissolved in a mixture of 50:50 methanol-acetone (v/v), and silica gel was added (3.0 g). After the removal of solvent with a rotary evaporator, the silica gel plug was loaded onto a column and eluted with 1:5 MeOH-CHCl3 (v/v). The fractions containing the required compound were evaporated under reduced pressure to afford the targeted compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Carbamimidic chloride hydrochloride, its application will become more common.

Reference:
Article; Shah, Khushbu; Queener, Sherry; Cody, Vivian; Pace, Jim; Gangjee, Aleem; Bioorganic and Medicinal Chemistry Letters; vol. 29; 15; (2019); p. 1874 – 1880;,
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1996-29-8, These common heterocyclic compound, 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, 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.

Reference Example-10 A solution of 1-bromo-4-chloro-2-fluoro benzene (10.0 g, 47.8 mmol) in THF was added dropwise to a suspension of magnesium (1.28 g, 52.5 mmol) in THF (50 mL) at 40 C. (oil bath temperature) in the presence of a catalytic amount of iodine in an argon gas atmosphere, whereby a Grignard reagent was prepared. The Grignard reagent was added dropwise to a solution of diethyl oxalate (8.37 g, 57.3 mmol) in THF at -50 C., and the temperature was slowly raised to room temperature, followed by stirring for 18 hours. After the reaction was completed, the reaction solution was poured into ice, then, acidified with concentrated hydrochloric acid, and the resultant product was extracted with ether (100 mL*2, 50 mL*1). The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure, whereby an orange oily crude product (12.9 g) was obtained. This was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), whereby ethyl 2-(4-chloro-2-fluorophenyl)-2-oxoacetate (4.17 g, yield: 41%) was obtained as a yellow oily material. 1H-NMR (400 MHz, CDCl3): delta1.40 (t, J=7.1 Hz, 3H), 4.43 (q, J=7.1 Hz, 2H), 7.22 (dd, J=1.8 and 10.2 Hz, 1H), 7.31 (dd, J=1.8 and 8.4 Hz, 1H), 7.89 (dd, J=7.6 and 8.4 Hz, 1H). 19F-NMR (376 MHz, CDCl3): delta-109 (s, 1F).

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 1996-29-8.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; SAGAMI CHEMICAL RESEARCH INSTITUTE; KOBAYASHI, Osamu; NIIKURA, Naoko; INOUE, Tomoko; MIZUTA, Satoshi; TAKATSUNA, Reiko; HIRAI, Kenji; SHIROUZU, Kentaro; OBATA, Miyoo; (183 pag.)US2016/24110; (2016); A1;,
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1871-57-4, Adding some certain compound to certain chemical reactions, such as: 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, 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 1871-57-4.

Step 1: methyl 14-cyclohex^l-7-meiksiotalene-7.&-dihydro-6H-indolol.2-e]fl.5]benzoxazocine-ll- carboxylate; To a solution of methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-lH-indole-6-carboxylate (prepared as described in example 9, step 1) in dry DMF (0.06 M) was added NaH (2.5 eq., 60% suspension in mineral oil). After 30 min, 3-chloro-2-(chloromethyl)prop-l-ene (1.2 eq.) was added dropwise via syringe and EPO the solution stirred at RT for 60 min. The reaction mixture was diluted with EtOAc and washed with IN aqueous HCl and with brine, dried (Na2SO4) and evaporated. The crude residue was purified by flash chromatography (10:1 PE/EtOAc), affording the pure methyl 14-cyclohexyl-7-methylene-7,8-dihydro- 6H-indolo[l,2-e][l,5]benzoxazocine-l l-carboxylate (70%) as light yellow foam; MS (ES+) m/z 402 (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 1871-57-4.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P ANGELETTI SPA; WO2006/46030; (2006); A2;,
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19393-92-1, A common heterocyclic compound, 19393-92-1, name is 2-Bromo-1,3-dichlorobenzene, molecular formula is C6H3BrCl2, 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 148 (7bR,11aS)-N-(2,6-dichlorophenyl)-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indol-6-amine An oven-dried three-necked round bottom flask was fitted with a septa, condenser, and a stopper. The flask was charged with tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H)-carboxylate from EXAMPLE 33, Part B (107 mg, 0.297 mmol), 2,6-dichlorobromobenzene (56 mg, 0.25 mmol), NaOt-Bu (71 mg, 0.74 mmol), and anhydrous toluene (6 mL). The solution was purged with argon at 80¡ã C. for 25 min then cooled to room temperature. While maintaining a blanket of argon, Pd2(dba)3 (5 mg, 6 mumol), and BINAP (7 mg, 12 mumol) were added quickly. The resulting mixture was heated to 80¡ã C. for 20 h under argon. After cooling to room temperature, the dark solution was diluted with ethyl ether (10 mL) and filtered through a pad of silica, washing with ether. The resulting solution was concentrated and the residue was chromatographed (10-12percent ethyl acetate in hexanes gradient) yielding an N-BOC intermediate (90 mg, 72percent) as a yellow foam: 1H NMR (300 MHz, CDCl3) delta 1.40 (s, 9H), 1.71-1.92 (m, 2H), 2.79-3.13 (m, 3H), 3.15-3.96 (m, 9H), 5.71 (s, 1H), 6.29-6.50 (m, 2H), 6.91-7.00 (s, 1H), 7.32 (d, 2H, J=8 Hz). This intermediate (90 mg, 0.18 mmol) was dissolved in dichloromethane (8 mL) and chilled in an ice bath. Trifluoroacetic acid (2 mL) was then added and the solution was stirred at room temperature for 2 h. The solution was made basic with 3 N NaOH, and extracted with dichloromethane. The organic layers were combined, dried over NaSO4 and concentrated to a yellow oil. An off-white solid was obtained upon trituration with ethyl acetate/hexanes yielding 58 mg (81percent) of the title compound of EXAMPLE 148. 1H NMR (300 MHz, CDCl3) delta 1.72-1.85 (m, 2H), 2.51-2.65 (m, 1H), 2.76-3.09 (m, 6H), 3.10-3.21 (m, 1H), 3.36-3.42 (m, 1H), 3.47-3.79 (m, 4H), 5.71 (s, 1H), 6.34 (s, 1H), 6.42 (s, 1H), 6.95 (t, 1H, J=8 Hz), 7.32 (d, 2H, J=8 Hz). LRMS (ES)+: 406 (M+H)+.

The synthetic route of 19393-92-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Robichaud, Albert; Fevig, John M.; Mitchell, Ian S.; Lee, Taekyu; Chen, Wenting; Cacciola, Joseph; US2002/173503; (2002); A1;,
Chloride – Wikipedia,
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104-11-0, The chemical industry reduces the impact on the environment during synthesis 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, I believe this compound will play a more active role in future production and life.

A solution of amine (70 mg, 0.45 mmol) and IBX (252 mg, 0.90 mmol) in 10 mL of CHCl3 was heated at reflux with vigorous stirring for 4 h. The resulting suspension was filtered and the filtrate was washed in sequence with 10% NaOH (5 mL x 3), 1 M HCl (5 mL x 3), and water. The organic layer was dried with MgSO4 and removed in vacuo to afford the desired product (60 mg, 94% yield). 1H NMR (400 MHz, 25 C, CDCl3): delta = 9.98 (s, 1H), 7.82 (d, 2H, J = 8.0 Hz), 7.51 (d, 2H, J = 8.0 Hz) ppm. 13C NMR (100 MHz, 25 C, CDCl3): delta = 186.22, 136.29, 130.01, 126.24, 124.79 ppm. ESI-MS: M + H+, found 141.7 (calc. 141.57).

The chemical industry reduces the impact on the environment during synthesis 1-(4-Chlorophenyl)-N-methylmethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chen, Li-Xia; Huang, Yin-Hui; Cong, Hang; Tao, Zhu; Chemical Papers; vol. 72; 3; (2018); p. 661 – 667;,
Chloride – Wikipedia,
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The chemical industry reduces the impact on the environment during synthesis 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, I believe this compound will play a more active role in future production and life. 104-11-0

General procedure: A solution of 0.17g (1.40mmol) of N-benzylmethylamine, 0.20g (1.40mmol) of K2CO3 and 0.40g of (R,S)-3(4-bromobutyl)-5-phenyloxazolidin-2-one 23 in ACN was allowed to stirring under reflux for 6-12h and monitored by TLC until the reaction was completed. The hot solution was filtered and concentrated in vacuo to afford 0.29g (85.0mmol) of a chromatography pure yellow oil 2a.

The chemical industry reduces the impact on the environment during synthesis 104-11-0. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zampieri, Daniele; Vio, Luciano; Fermeglia, Maurizio; Pricl, Sabrina; Wuensch, Bernhard; Schepmann, Dirk; Romano, Maurizio; Mamolo, Maria Grazia; Laurini, Erik; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 712 – 726;,
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The chemical industry reduces the impact on the environment during synthesis 823-57-4, name is 2-Bromo-5-chloroaniline, I believe this compound will play a more active role in future production and life. 823-57-4

Compound 37b (4.2 g, 20.3 mmol) is melted at 500C in a 100 mL round-bottomed flask containing a stirring bar and immersed in an oil bath. A solution of zinc chloride (700 mg, 5.03 mmol) and ferric chloride (540 mg, 3.25 mmol) in 3.3 mL of water is added in one portion followed by 20 m L of absolute EtOH. The flask is stoppered with a rubber septa and a needle is inserted to avoid any pressure build-up. The mixture is warmed to 800C and acrolein (1.68 mL, 24.4 mmol) is added via a syringe pump over a 2 h period. After the addition, the mixture is stirred at 800C for 1 h and an additional amount of solid ferric chloride is added (4.1 g, 25.3 mmol). The mixture is stirred at 8O0C for about an extra 24 h and then concentrated under vacuum to give a semi-solid residue. 200 mL of water is added followed by a 10 N aqueous solution of NaOH (20 mL) and 200 mL of CH2CI2. After shaking the mixture for a few minutes, the solid is filtered over a pad of Celite.(R). and the filtrate is transferred into a separatory funnel. The organic layer is separated and the aqueous layer is extracted with CH2CI2. The combined organic extracts are washed with brine, dried (Na2SO4), filtered and concentrated under vacuum to give 3.69 g of a brown solid. This solid is triturated in hot CH3CN and filtered. The solid is discarded and the filtrate is concentrated under vacuum to give 2.3 g of a brown semi-solid. This material is purified on a CombiFlash.(R). Companion apparatus on 40 g silica gel column eluted with EtOAc/hexanes gradient. After evaporation of the solvent 13-152under vacuum, the desired compound 37c is isolated as a yellow solid (390 mg, 8percent yield).

The chemical industry reduces the impact on the environment during synthesis 823-57-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; WO2009/62308; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 2613-34-5, name is 3-Chloro-2,4-difluoroaniline, 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. 2613-34-5

3-CHLORO-2, 4-DIFLUOROANILINE (1.7 g, 10.1 mmol) and 5N hydrogen chloride in isopropanol (2 ml) were added to a suspension of tert-butyl 4- [ (4-CHLORO-7-METHOXYQUINAZOLIN-6- yl) oxy] PIPERIDINE-1-CARBOXYLATE (4 g, 10.1 mmol, PCT Int. Appl. W02003082831, AstraZeneca) in isopropanol (50 ml). The mixture was stirred at 80C for 3 hours. After evaporation of the solvents, the residue was purified by chromatography on silica gel (eluant: 5-10% 7N methanolic ammonia in dichloromethane) to give 4- (3-CHLORO-2, 4-difluoroanilino) – 7-METHOXY-6-[(PIPERIDIN-4-YL) OXY] QUINAZOLINE (3.63 g, 85%) as a white solid. HNMR Spectrum: (CDC13 + CD3CO2D) : 2.15 (m, 2H), 2.30 (m, 2H), 3.34 (m, 2H), 3.47 (m, 2H), 4.01 (s, 3H), 4.91 (m, 1H), 7.03 (m, 1H), 7.58 (m, 2H), 7.90 (s, 1H), 8.55 (s, 1H) ; Mass spectrum: MH+ 421.

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 2613-34-5.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/28470; (2005); 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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., 1996-30-1

2-fluoro-5-chlorobromobenzene 18a (11.0g, 52.8mmol), ethynyltrimethyl Silane (7.7 g, 79 mmol) and triethylamine (60 mL) were mixed, and then cuprous iodide (100 mg, 0.53 mmol) and ditriphenylphosphine palladium chloride (1.86 g, 2.65 mmol) were added.The reaction mixture was heated to 80 C under a nitrogen atmosphere and stirring was continued for 4 hours.After the reaction was completed, the solution was desolvated under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 100/1) to obtain the target product ((2-fluoro-5-chlorophenyl) ethynyl) trimethyl. Silane 18b (11.0 g, yellow oil), yield: 90%.

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; BEIJING TIANCHENG PHARMA CO., LTD.; CHEN, XIANGYANG; GAO, YINGXIANG; KONG, NORMAN XIANGLONG; (118 pag.)TW2019/38538; (2019); A;,
Chloride – Wikipedia,
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363-51-9, These common heterocyclic compound, 363-51-9, name is 2-Chloro-6-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.

Acetic anhydride (10 mL, 106 mmol) was added to a solution of 2-chloro-6-fluoroaniline (12.81 g, 88 mmol) in AcOH (44 mL) and the mixture was stirred at 90 C. for 2 hrs. After cooling to r.t., water was added and the solid precipitate was collected by filtration, washed with water, and air dried to afford N-(2-chloro-6-fluorophenyl)acetamide (16.2 g, 98% yield) as a white solid. The crude product obtained was used directly in the next step without further purification. LCMS calculated for C8H8ClFNO (M+H)+: m/z=188.0; Found 188.0.

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 363-51-9.

Reference:
Patent; Incyte Corporation; Hummel, Joshua; Vechorkin, Oleg; Sokolsky, Alexander; Ye, Qinda; Liu, Kai; Yao, Wenqing; (60 pag.)US2020/48241; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics