FIELD: chemistry.
SUBSTANCE: invention relates to organic chemistry and particularly to a method of producing 1-chloroadamantyl-3-carboxylica acid amide used in synthesis of 1,3-disubstituted adamantane derivatives and as starting material when producing medicinal agents. The method involves simultaneous chlorination and amidation of adamantyl-1-carboxylic acid or acid chloride thereof with chlorinating agents and acetonitrile in the presence of a catalyst, where the chlorinating agent used is carbon tetrachloride and the catalyst is VO(acac)2, in the presence of water at temperature 125-150°C for 1-3 hours in molar ratio [VO(acac)2] : [Ad-R] : [CH3CN] : [H2O] : [CCl4] = 1 : (100-1000) : (100-1000) : (100-1000) : (200-2000), where (R-COOH, COCl).
EFFECT: achieving high output (95%) of 1-chloroadamantyl-3-formamide with 100% conversion of adamantyl-1-carboxylic acid or acid chloride thereof.
1 cl, 15 ex, 1 tbl
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Authors
Dates
2012-07-10—Published
2010-02-08—Filed