Tag: M.W=100-200

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. 772-49-6, name is 1-Chloro-3-(trifluoromethoxy)benzene, A new synthetic method of this compound is introduced below., COA of Formula: C7H4ClF3O

N,N-Di-isopropylamine (38.4 ml, 27lmmol) was added dropwise to a solution of nbutyllithium (1.6 M, 169 ml, 271 mmol) in THF (180 ml) at 0C and the reaction mixture was stirred and allowed to warm to room temperature over 30 mins. The LDA solution was then added drop wise over lOminutes to a solution of 1-chloro-3- (trifluoromethoxy)benzene (50 g, 246 mmol) in THF (500 ml) at -70C and the resultingmixture was stirred at -70C for 30 minutes. Finally N,N-dimethylformamide (23 ml, 296 mmol) was added dropwise and the resultant mixture stirred at -70C for 30 minutes.The reaction was quenched at -70C by addition of NH4C1 (saturated aqueous solution) to pH 7-8 and the resulting mixture was extracted with EtOAc (3 x 75 ml). The combined organic phases were washed with water (100 ml), brine (100 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound (55 g, 99% yield).LCMS (Method 16, ES+) RT 1.32 mm., 224 [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; UCB BIOPHARMA SPRL; SANOFI; DE HARO GARCIA, Teresa; DELIGNY, Michael; HEER, Jag Paul; QUINCEY, Joanna Rachel; XUAN, Mengyang; ZHU, Zhaoning; BROOKINGS, Daniel Christopher; CALMIANO, Mark Daniel; EVRARD, Yves; HUTCHINGS, Martin Clive; JOHNSON, James Andrew; JADOT, Sophie; KEYAERTS, Jean; MAC COSS, Malcolm; SELBY, Matthew Duncan; SHAW, Michael Alan; SWINNEN, Dominique Louis Leon; SCHIO, Laurent; FORICHER, Yann; FILOCHE-ROMME, Bruno; (365 pag.)WO2016/50975; (2016); A1;,
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These common heterocyclic compound, 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, 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. Formula: C8H10ClN

EXAMPLE 22 Under a static nitrogen atmosphere at 0 C., a solution of n-butyllithium (7.87 g, 0.123 mol) in hexane was added to a solution of tetramethylethylenediamine (14.3 g, 0.123 mol) in 60 ml. of anhydrous cyclohexane with constant stirring. The resulting mixture was stirred for an additional 15 minutes and then cooled to -70 C. using a solid carbon dioxide-acetate bath. A solution of N-methyl-4-chloro-benzylamine (9.6 g, 0.06 mol) in 60 ml. of anhydrous cyclohexane was added to the reaction mixture to produce a suspension containing a dilithio compound. This suspension was stirred for 2 hours at 26 C. and then cooled to -70 C. using a solid carbon dioxide-acetone bath. A solution of phenylphosphonic dichloride (12.5 g, 0.064 mol) in 60 ml. of anhydrous cyclohexane was rapidly added to the suspension causing the temperature of the reaction to increase to -20 C. The reaction mixture was allowed to cool to -70 C., after which time the solid carbon dioxide-acetone bath was removed and the reaction mixture was stirred for 2.5 hours. The reaction mixture was cooled to 0 C. and then quenched with the rapid addition of 12 ml. of acetic acid. The cyclohexane was removed on a rotary evaporator, and the resulting residue was partitioned between methylene chloride and water. The layers were separated and the methylene chloride layer was dried over magnesium sulfate and concentrated in vacuo to yield a red oil. Distillation of the red oil at 180 C. and 0.25 mm yielded a yellow solid which was slurried in ether to yield 1-phenyl-2-methyl-6-chloro-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide (2.2 g, 13% yield) as a pale yellow solid having a melting point of 159-162 C. and the following analysis: Calculated: C, 60.55; H, 4.72; N, 5.04. Found: C, 60.59; H, 4.72; N, 5.06.

The synthetic route of 1-(4-Chlorophenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Monsanto Company; US4319913; (1982); A;,
Chloride – Wikipedia,
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Reference of 2687-12-9,Some common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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 representative procedure of skeleton 4 is as follows: K2CO3 (400 mg, 2.9 mmol) was added to a solution of 3 (1.0 mmol) in acetone (10 mL) at rt. The reaction mixture was stirred at rt for 10 min. Cinnamyl chloride (1.05 mmol) was added to the reaction mixture at rt. The reaction mixture was stirred at reflux for 8 h. The reaction mixture was cooled to rt, concentrated, and extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried, filtered, and evaporated to afford crude product under reduced pressure. Purification on silica gel (hexanes/EtOAc=6:1 to 1:1) afforded 4.

The synthetic route of 2687-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chang, Meng-Yang; Lu, Yi-Ju; Cheng, Yu-Chieh; Tetrahedron; vol. 71; 8; (2015); p. 1192 – 1201;,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, 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 1871-57-4, SDS of cas: 1871-57-4

[0129] A mixture of BnNH-L-Asp(Otbutyl)-Obn from step 1a (12.1 g, 32.6 mmol), K2CO3 (14 g, 3 eq.), NaI (3.0 g, 20mmol) and 1-chloro-2-chloromethyl-1-propene (5.1 g, 40.8 mmol) in MeCN (150 mL) was stirred at 81 C for 16 h. Aftercooling, the mixture was filtered. The filtrate was concentrated and purified by Combiflash (hexane and ethyl acetate:gradient 0 to 8% during 12 min) to give (8.7 g) 1-benzyl 4-tert-butyl (2S)-2-{benzyl[2-(chloromethyl)prop-2-en-1-yl]amino}succinate, MS (ESI): 458.3/460.3 (M + H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-2-chloromethyl-1-propene, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; YAO, Wenqing; ZHOU, Jincong; XU, Meizhong; ZHANG, Fenglei; METCALF, Brian; EP1622569; (2015); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 57946-56-2, name is 4-Chloro-2-fluoroaniline, 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 57946-56-2, Safety of 4-Chloro-2-fluoroaniline

Hydrogen chloride (6.5 M, 2.54 mL) was added to a mixture of compound 1 (4.51 g, 15.0 mmol) and 4-chloro-2-fluoroaniline (2.40 g, 16.5 mmol) in 2-propanol (160 mL), then the mixture was heated at reflux for 2 h. The mixture was cooled and solid was filtered. The solid was then washed with 2-propanol, followed by Et2O, and dried under vacuum overnight to give 2a (7.9 g, 94%) as a white solid.

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:
Article; Gao, Mingzhang; Lola, Christian M.; Wang, Min; Miller, Kathy D.; Sledge, George W.; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3222 – 3226;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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 2533-69-9, COA of Formula: C3H4Cl3NO

General procedure: Preparation of 2-methyl-6-nitro-2H-indazole (5d). To a stirred mixture of 6-nitro-1H-indazole (1.0 g, 0.0061 mmol) in dichloromethane (25.0 mL) was added trifluoromethanesulfonic acid (0.54 mL, 0.0061 mmol), stirred for 5-10 min at 25-35 C. To this mixture was added methyl 2,2,2,-trichlroacetimidate (2.69 g, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16-18 h under N2. After reaction completion, chilled saturated NaHCO3 solution was added. The aqueous and organic phases were separated. Aqueous phase was extracted with dichloromethane 10 mL. Combined organic layers were washed with DM water (2 × 10 mL). Organic layer was dried over anhydrous Na2SO4, filtered, and evaporated completely under vacuum to obtain 2-methyl-6-nitro-2H-indazole (1.03 g, 95.0%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 8.683 (s, 1H), 8.03 (s, 1H), 7.91 (d, 1H), 7.89 (d, 1H), 4.31 (s, 3H); 13C NMR (400 MHz, CDCl3) 146.93, 146.46, 124.52, 121.24, 115.70, 115.27, 41.06; MS (+ve ES) 178 (M+H).

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:
Article; Baddam, Sudhakar Reddy; Uday Kumar; Panasa Reddy; Bandichhor, Rakeshwar; Tetrahedron Letters; vol. 54; 13; (2013); p. 1661 – 1663;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 4152-90-3, These common heterocyclic compound, 4152-90-3, name is (3-Chlorophenyl)methanamine, 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.

N-(3-Chlorobenzyl)-5-fluoro-2-nitrobenzenamine:; 2,4-Difluoronitrobenzene (2.9 g, 18.1 mmol), 3-chlorobenzylarnine (2.6 g, 18.1 mmol) 0 and LambdazetaiV-diisopropylethylamine (2.4 g, 18.1 mmol) were stirred in acetonitrile (25 mL) at room temperature for 2 hours. The solvent was evaporated and the crude mixture was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated in vacuo to collect the title compound (4.8 g, 95 percent yield). 1H NMR (400 MHz, CDCl3): delta 8.55 (s, IH), 8.25 (dd, IH), 7.32-7.21 (m, 4H), 6.41 (m, 2H), 4.50 (d, 2H).

The synthetic route of 4152-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PREDIX PHARMACEUTICALS HOLDINGS, INC.; WO2006/81332; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 26487-67-2, A common heterocyclic compound, 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, molecular formula is C8H17Cl2N, 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.

Add sodium hydride (18 g, 0.45 mol) into a solution of 4-benzyloxylphenol (41 g, 0.20 mol) and 2- (hexamethyleneimino) ethyl chloride hydrochloride (44 g, 0.22 mmol) in THF (600 mL) and DMF (100 mL) at room temperature. Heat to 60°C for 30 minutes. Pour the solution into ice and water. Dilute with ethyl acetate (500 mL) and separate layers. Dry the organic layer with magnesium sulfate, filter and concentrate under reduced pressure to give brown oil. Dissolve the oil in ethyl acetate (500 mL) and methanol (500 mL). Add ammonium formate (100 g, 1.59 mol) and palladium on carbon (10 g, 9.4 mmol). Heat the mixture to reflux for 30 minutes. Add ammonium formate (100 g, 1.59 mol) and palladium on carbon (10 g, 9.4 mmol). Heat the reaction mixture for 30 minutes. Filter the supension through a pad of celite and elute with ethyl acetate (500 mL). Evaporate solvent under reduced pressure and add water (100 mL). Dilute the mixture with ethyl acetate (500 mL) and separate layers. Wash the organic layer with saturated sodium bicarbonate solution (2 x 200 mL), dry with magnesium sulfate, filter and evaporate solvent under reduced pressure to give 31 g (64 percent) of4- (2-azepan-l-yl- ethoxy)-phenol. Combine 2-benzyloxy-1-bromo-6-methoxy-naphthalene (31 g, 90 mmol), 4- (2- azepan-l-yl-ethoxy)-phenol (31 g, 132 mmol), copper bronze (12 g, 189 mmol), potassium carbonate (25 g, 181 mmol) and pyridine (400 mL). Heat the reaction mixture to reflux for 85 hours. Cool and filter the residue with celite and elute with methanol and methylene chloride (500 mL, Vu = 1 : 5). Evaporate solvent under reduced pressure and chromatograph the residue on a silica gel column eluting the material with a step gradient of methanol/dichloromethane (0 to 10percent) to get 19 g (43percent) of 1- {2- [4- (2-benzyloxy-6- meCoxy-naphthalen-l-yloxy)-phenoxyl-ethyl}-azepane. Dissolve 1- {2- [4- (2-benzyloxy-6-methoxy-naphthalen-1-yloxy)-phenoxy]-ethyl}- azepane (19 g, 38 mmol) in ethyl acetate (500 mL) and methanol (600 mL). Heat the mixture to obtain a clear solution. Cool to room temperature. Add ammonium formate (30 g, 476 mmol) and palladium on carbon (2 g, 1. 9 mmol). Heat to reflux for 30 minutes. Add ammonium formate (7 g, 111 mmol) and palladium on carbon (0.7 g, 0.7 mmol). Heat to reflux for 30 minutes. Filter the supension through a pad of celite and elute with ethyl acetate (500 mL). Evaporate solvent under reduced pressure and add water (100 mL). Dilute the mixture with ethyl acetate (500 mL) and separate layers. Wash the organic layer with saturated sodium bicarbonate solution (2 x 200 mL), dry with magnesium sulfate, filter and evaporate solvent under reduced pressure to give 15.1 g (97percent) of 1- [4- (2-azepan-1-yl-ethoxy)-phenoxy]-6-methoxy-napbthalen-2-ol. Add trifluoromethanesulfonic anhydride (7 mL, 42 mmol) into a solution of 1- [4- (2-azepan-1-yl-ethoxy)-phenoxy]-6-methoxy-naphthalen-2-ol (15 g, 37 mmol), triethylamine (20 mL) and methylene chloride (500 mL) at-50°C. Warm the reaction mixture to room temperature and stir for 1 hour at that temperature. Cool the reaction mixture to-78°C and add brine (20 mL). Warm the reaction to room temperature. Separate layer and wash the organic layer with saturated sodium bicarbonate solution (100 mL) and brine. Dry the organic layer with magnesium sulfate, filter and evaporate solvent under reduced pressure. Chromatograph the residue on a silica gel column eluting the material with a step gradient of methanol/dichloromethane (0 to 10percent) to get 20 g (99percent) of trifluoro-methanesulfonic acid 1- [4-(2-azepan-1-yl-ethoxy)-phenoxy]-6-methoxy- naphthalen-2-yl ester.

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73204; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 202925-07-3, name is 2-Chloro-1-fluoro-4-methoxybenzene, 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 2-Chloro-1-fluoro-4-methoxybenzene

To 2-chloro-1-fluoro-4-methoxybenzene (5 g) in methylene chloride (30 ml) solution, titanium tetrachloride (5.8 ml) and alpha,alpha-dichloromethylmethylether (2.8 ml) were added under ice cooling, the mixture was stirred at 2C for 11.5 hours, then the reaction solution was poured into ice. Next, the methylene chloride layer was separated, washed with saturated saline, dried over with anhydrous sodium sulfate, and concentrated. The obtained residue was recrystallized from ethylether. The thus obtained 4-chloro-5-fluoro-2-methoxybenzaldehyde (3.41 g) was used instead of the starting material in Reference Example 2, that is, the compound S1, for successively the similar procedure as in Reference Example 2 to Reference Example 6 to obtain the title compound. NMR (CDCl3): delta7.96(1H, s), 7.37(1H, d, J=9.0Hz), 7.06(1H, br), 6.96(1H, d, J=5.9Hz), 4.33(2H, d, J=6.1Hz), 3.84(3H, s) MS: 378(M+Na)+

The synthetic route of 2-Chloro-1-fluoro-4-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asubio Pharma Co., Ltd.; Daiichi Sankyo Company, Limited; EP2025672; (2009); A1;,
Chloride – Wikipedia,
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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 1939-99-7 as follows. name: Phenylmethanesulfonyl chloride

To a solution of 2-((tert-butyldimethylsilyl)oxy)ethanamine (11.7 g, 66.6 mmol) and triethylamine (11.2 mL, 79.9 mmol) in tetrahydrofuran (222 mL) at 0 C. was slowly added phenylmethanesulfonyl chloride (12.7 g, 66.6 mmol) portion wise and the reaction was stirred at room temperature for 16 hours. MTBE was then added and the Et3N.HCl salt was removed by filtration. The filtrate was then concentrated and purified by silica gel column chromatography (0-30% Acetone in heptane, 216 nM) to N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-phenylmethanesulfonamide (17.8 g, 81% yield). LCMS (ESI), m/z, 330. [M+H]+.

According to the analysis of related databases, 1939-99-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Fauber, Benjamin; Gobbi, Alberto; Rene, Olivier; Bodil van Niel, Monique; Gancia, Emanuela; Gaines, Simon; Laddywahetty, Tammy; Vesey, David; Ward, Stuart; Winship, Paul; US2015/197529; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics