Method for synthesizing n-thiobenzyl imine or its derivatives by bunte salt

Abstract

The invention discloses a method for synthesizing N-thiobenzyl imine or its derivatives from Bunte salt. The method uses benzylamine or benzylamine derivatives and Bunte salt as raw materials, uses cuprous bromide as a catalyst, and uses N,N-dimethylformamide as a solvent to fully react at 70 to 90°C. , the reaction solution is separated and purified to obtain N-thiobenzyl imine or its derivatives. The method of the invention is simple and safe, does not require the presence of oxidants and additives, adds cuprous bromide as a catalyst, reduces the reaction temperature, improves the reaction yield, avoids the use of raw materials such as mercaptan with bad smell, has less three wastes, and is environmentally friendly.

Description

technical field

[0001] The invention belongs to the technical field of organic synthesis, and relates to a method for synthesizing N-thiobenzyl imine or derivatives thereof from Bunte salt (organic thiosulfate).

[0002] technical background

[0003] N-thiobenzyl imine derivatives, also known as thioximes, are important synthetic intermediates in the field of organic synthesis, widely used in N-sulfinimide, N-sulfonimide, β-lactam , N-vinyl formamide and other bio-organic molecules in the synthesis. The sulfur sources used in the reported synthetic methods are mainly N-(thio)phthalimide, sulfenamide, thiophenol and disulfide. E.g:

[0004] Document 1 (Jordi Burés, Carles Isart, and Jaume Vilarrasa, Efficient Preparation of N-Phenylsulfenyl Ketimines from Oximes or Nitro Compounds without Racemization of α-Stereocenters [J]. Organic letters, 2007, 9, 4635-4638.) uses oxime and N- (thio)phthalimide, with trimethylphosphine (PMe 3 ) as a reducing agent, using tetrahydrofuran...

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