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A kind of synthetic method of 1-amino-1-cyclopropanenitrile hydrochloride

A technology of cyclopropanenitrile hydrochloride and synthesis method is applied in the field of synthesis of 1-amino-1-cyclopropanenitrile hydrochloride, can solve problems such as unknown yield, achieve low cost, high yield and reaction conditions mild effect

Inactive Publication Date: 2020-09-22
JIANGSU CANCER HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] 1-Amino-1-cyclopropanenitrile is an important organic intermediate, and its currently disclosed synthetic methods are: 1990, Salaun, Jacques (Journal of Organic Chemistry, 1990, 55(14), 4276-81.) It is reported that acrolein is used as a raw material to prepare 1-amino-1-cyclopropanenitrile through a series of reactions, and a highly toxic cyanide is used in the middle; in 2013, Shivaraj, Yellappa (Journal of the Korean Chemical Society, 57(2), 241-245; 2013) reported the preparation of 1-amino-1-cyclopropanenitrile by using cyclopropanone as a raw material through a series of reactions; ), 5164-5171; 2015) no specific steps to refer to, and the yield is unknown; 2005, Link, John O. et al. (PCT Int. Appl., 2005028429, 2005074904), 2006, Woo, Soon H. et al. (PCT Int. Appl., 2006060810), Setti, Eduardo L. et al. (PCT Int. Appl., 2006060494), Mossman, Craig J. et al. (PCT Int. Appl., 2006102535), 2008 Link, John O . et al (PCT Int. Appl., 2008042968), Link, John O. et al (U.S. Pat. Appl. Publ., 20080293819), 2009 Link, John O. et al (U.S. Pat. Appl. Publ., 20080293819), in 2010 Hart, Barry et al. (PCT Int. Appl., 2010056877), in 2012 Adams, Nicholas D. et al. (PCT Int. Appl., 2012064642) reported the use of benzophenone imine and aminopropyl Nitrile is reacted in dichloromethane, then reacted with 1,2-dibromoethane in the presence of a phase transfer catalyst in toluene to produce benzophenone iminoacetonitrile, and finally reacted in a two-phase system of aqueous hydrochloric acid and ether Obtain aminopropionitrile hydrochloride; same as the starting material of the above method, the method of slightly improved processing method is Zhang Huaxing et al. (CN 101225057B), (Guangdong Huagong, 36(6), 35-36; 2009) Reported reaction of benzophenone imine with aminopropionitrile Diphenylcuprous imine acetonitrile reacts with 1,2-dibromoethane under alkaline conditions to generate diphenylcuprous imine cyclopropionitrile, which is then decomposed by acidic cation exchange resin to remove benzophenone imine Protection, the deprotected amino group reacts with the sulfonic acid group in the cationic resin, the product is immobilized in the resin, and the product is separated from the substrate by filtration, and the resin loaded with the product is deprotected under alkaline conditions to obtain 1- Amino-1-cyclopropanenitrile

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0017] Add 560 mL of diisopropylethylamine, 56 g of aminoacetonitrile and 352 g of benzenesulfonyl chloride into the reaction flask, and react under reflux. After monitoring the reaction, diisopropylethylamine is recovered by distillation under reduced pressure, and the residue is poured into water , extracted three times with chloroform, combined the chloroform phases, washed with water, dried over anhydrous magnesium sulfate, filtered, and spin-dried to obtain 330 g of N,N-diphenylsulfonylacetonitrile with a yield of 98.2%.

[0018] Add 330 g of N,N-diphenylsulfonylacetonitrile and 660 mL of N,N-dimethylacetamide into the reaction flask, cool to 0°C, and slowly add 59 g of sodium hydride with a mass percentage of 80%, Stir at 0°C for 30 min, slowly add 185 g of 1,2-dibromoethane dropwise, after the reaction, slowly pour the mixed system into the ice-water mixture, extract three times with chloroform, combine the chloroform phases, wash with water, dry, spin After drying, 348...

Embodiment 2

[0021] Add 280 mL of diisopropylethylamine, 56 g of aminoacetonitrile, and 352 g of benzenesulfonyl chloride into the reaction flask, and react under reflux. After monitoring the reaction, diisopropylethylamine is recovered by distillation under reduced pressure, and the residue is poured into water , extracted three times with chloroform, combined the chloroform phases, washed with water, dried over anhydrous magnesium sulfate, filtered, and spin-dried to obtain 330 g of N,N-diphenylsulfonylacetonitrile with a yield of 98.2%.

[0022] Add 330 g of N,N-diphenylsulfonylacetonitrile and 1320 mL of N,N-dimethylformamide into the reaction flask, cool to 0°C, and slowly add 59 g of sodium hydride with a mass percentage of 80%, Stir at 0°C for 30 min, slowly add 185 g of 1,2-dibromoethane dropwise, after the reaction, slowly pour the mixed system into the ice-water mixture, extract three times with chloroform, combine the chloroform phases, wash with water, dry, spin After drying, 3...

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Abstract

The invention discloses a synthesis method of 1-amino-1-cyclopropanecarbonitrile hydrochloride. The method includes: using aminoacetonitrile as the starting material to react with benzene sulfonyl chloride to obtain N, N-dibenzenesulfonyl acetonitrile, further carrying out ring closing reaction with 1, 2-dibromoethane under a sodium hydride alkaline condition to obtain N, N- benzenesulfonamidocyclopropanecarbonitrile, and finally conducting deprotection of benzoyl under an acidic condition so as to obtain 1-amino-1-cyclopropanecarbonitrile hydrochloride. The method provided by the invention has the advantages of mild reaction conditions, high yield and low cost, and is suitable for industrial application.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 1-amino-1-cyclopropanenitrile hydrochloride. Background technique [0002] 1-Amino-1-cyclopropanenitrile is an important organic intermediate, and its currently disclosed synthetic methods are: 1990, Salaun, Jacques (Journal of Organic Chemistry, 1990, 55(14), 4276-81.) It is reported that acrolein is used as a raw material to prepare 1-amino-1-cyclopropanenitrile through a series of reactions, and a highly toxic cyanide is used in the middle; in 2013, Shivaraj, Yellappa (Journal of the Korean Chemical Society, 57(2), 241-245; 2013) reported the preparation of 1-amino-1-cyclopropanenitrile by using cyclopropanone as a raw material through a series of reactions; ), 5164-5171; 2015) no specific steps to refer to, and the yield is unknown; 2005, Link, John O. et al. (PCT Int. Appl., 2005028429, 2005074904), 2006, Woo, Soon H. et al. (PCT...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/30C07C255/46
CPCC07C253/30C07C303/38C07C303/40C07C255/46C07C311/20C07C311/19
Inventor 崔振海陈静
Owner JIANGSU CANCER HOSPITAL
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