Author: Jessica.F

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

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

Synthetic Route of 24279-39-8, 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. 24279-39-8, name is 2,6-Dichloro-4-(trifluoromethyl)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 6; Ethyl 2- {5-amino-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazol-4- YL} CYCLOPROPANECARBOXYLATE; To a stirred solution OF 2, 6-DICHLORO-4- (TRIFLUOROMETHYL) PHENYLAMINE (3.0 g, 13 mmol) in ethanol (3 MT) at–5C was added TETRAFLUOROBORIC acid (48% in water, 27.3 MINOT). To the mixture was added isoamyl nitrite (1.8 ml, 13. 6 MMOL), dropwise over 10 min, and the reaction mixture was stirred for 30 min at room temperature. The solid was filtered and WASHED-WITB ETHANOL, followed by diethyl ether,. to give. the diazonium salt (3.2g, 9. 73 NIMOL, 75%) as a white solid. To a solution of Preparation 6 (50 mg, 0.20 mmol) in acetonitrile (2 ml) at 0C was added diazonium-salt (65 mg, 0.20 mmol). The reaction mixture was then allowed to warm to room temperature with stirring. The solution was concentrated under a stream of nitrogen and to the residue was added dichloromethane (2. 5 ml), ammonia (0.880, 2.5 ml) and water (2.5 ml), with vigorous stirring. The. mixture was partitioned between water (20 ml) and dichloromethane- (20 ml) and the two layers were separated. The aqueous layer was extracted with dichloromethane (2 X 10 ml) and the combined organic layers were dried (NA2SO4) and concentrated in vacuo. The residue was loaded on to an ABSOLUTE column (silica, 2 g) in a mixture of cyclohexane and dichloromethane mixture (4 :-1) and eluted with cyclohexane : ethyl acetate [1 : 0 to 3 : 7]. The appropriate fractions were combined and concentrated to give the product (15 mg, 0, 03 mmol, 17 %) as an orange oil. MS (ES) M/Z [MH+]. = 433. 42,. C17H13C12F3N402 +H REQUIRES 433. 04459. NMR (CDC13, selected data): 1.35 (t, 3H), 1.6-1. 7 (m, 2H), 1. 9- 2.0 (m, 1H), 2.0-2. 1 (m, 1H), 3.65 (S, 2H), 4. 2 (q, 2H), 8.8 (M, 2H).

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, 2,6-Dichloro-4-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/23773; (2005); A1;,
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

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

Electric Literature of 174913-12-3, A common heterocyclic compound, 174913-12-3, name is 1-Bromo-3-chloro-5-methoxybenzene, molecular formula is C7H6BrClO, 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.

Preparation 3 [3-CHLORO-5-METHOXVBENZONITRILE] Tetrakis (triphenylphosphine) palladium (0) (174 mg, 0.15 [MMOL)] was added in one portion to a stirred solution of the bromide of Preparation 1 (500 mg, 2.26 [MMOL)] and zinc cyanide (146 mg, 1.24 [MMOL)] [IN N, N-DIMETHYLFORMAMIDE] (3 ml) at room temperature under a nitrogen atmosphere. The reaction was heated at [100C] for 14 hours and then cooled to room temperature. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel using ethyl acetate in cyclohexane as eluant (5: 95) to provide the title compound as a yellow oil (380 mg).1H-NMR [(300MHZ,] [CDC13)] : [8 3.] 82 (s, 3H), 7.04 (s, [1H),] 7.12 (s, [1H),] 7.23 (s, 1H).

The synthetic route of 174913-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/31178; (2004); 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. 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 63624-28-2

General procedure: To a solution of 0.5 mL of pyridine and 0.5 mmol of intermediate 5,20 mL of dried dichloromethane was added followed by 1 mmol of selectedsubstituted sulfonyl chlorides (a-k). The resulting reaction mixturewas refluxed for 12-17 h and reaction was monitored by TLC. Aftercompletion, the reaction mass was quenched using 20 mL of 10% NaOHfollowed by the extraction with chloroform with quantities 3×15 mL.The organic portion was then passed through anhydrous sodium sulfate,concentrated in vacuo and purified by column chromatography (DCM)to afford 7a-k.

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 63624-28-2.

Reference:
Article; Patel, Rahul V.; Mistry, Bhupendra M.; Syed, Riyaz; Parekh, Nikhil M.; Shin, Han-Seung; Bioorganic Chemistry; vol. 87; (2019); p. 23 – 30;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 771583-81-4, 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. 771583-81-4, name is 4-Chloro-2-(trifluoromethyl)benzylamine, This compound has unique chemical properties. The synthetic route is as follows.

5-((4- (ethylsulfonyl) benzyl) carbamoyl) -2-methoxybenzoic acid (150.0 mg, 0.4 mmol), HATU (302.2 mg, 0.8 mmol) and DIPEA (154.1 mg, 1.2 mmol) was dissolved in tetrahydrofuran (10 mL), and after stirring at room temperature for 0.5 hours, 4-chloro-2- (trifluoromethyl) benzylamine (125.0 mg, 0.6 mmol) was added, and the reaction was performed at room temperature for 4 hours. An appropriate amount of water was added and extracted three times with ethyl acetate. The organic phases were combined and washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The concentrate was purified by preparative high performance liquid chromatography to obtain the title compound (90.0 mg, yield: 38%).

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-2-(trifluoromethyl)benzylamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Liu Chunchi; Liu Jinming; Ren Yun; Cai Jiaqiang; Wang Lichun; Wang Jingyi; (42 pag.)CN110724075; (2020); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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

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,
Chlorides – an overview | ScienceDirect Topics