FIELD: chemistry.
SUBSTANCE: invention relates to a method of producing 1-chloro-3-cyanoadamantane of formula (I), which can be used in synthesis of biologically active 1,3-disubstituted adamantane derivatives and also as an intermediate in synthesis of medicinal agents. The method involves reaction of adamantyl-1-carboxylic acid or acyl chloride thereof with acetonitrile or tetrachloromethane in the presence of a vanadium catalyst VO(acac)2 in molar ratio [VO(acac)2]:[Ad-R]:[CH3CN]:[CCl4] = 1:(100-1000):(100-1000):(100-2000) (R = COOH, COCl), temperature 125-150°C for 1-3 hours.
EFFECT: method enables to obtain 1-chloro-3-cyanoadamantane with high output and 100% conversion of adamantyl-1-carboxylic acid or acyl chloride thereof.
1 tbl, 2 ex
Title | Year | Author | Number |
---|---|---|---|
METHOD OF PRODUCING 1-CHLOROADAMANTYL-3-FORMAMIDE (1-CHLOROADAMANTYL-3-CARBOXYLIC ACID AMIDE) | 2010 |
|
RU2455282C2 |
METHOD OF PRODUCING ADAMANTANOL-1 | 2010 |
|
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METHOD OF PRODUCING 1-ACETYLADAMANTANE | 2008 |
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RU2408571C2 |
METHOD OF PRODUCING 1-CHLOROADAMANTANE | 2011 |
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RU2486169C2 |
METHOD OF PRODUCING 1-ACETYLADAMANTANE | 2008 |
|
RU2440326C2 |
METHOD OF PREPARING 1-CHLORO-3-ACETYL- AND 1-CHLORO-1,3-DIACETYLADAMANTANES | 2000 |
|
RU2197467C2 |
METHOD OF PRODUCING 1,3-DICHLOROADAMANTANE | 2011 |
|
RU2459797C1 |
METHOD OF PRODUCING N-(1-ADAMANTYL)ACETAMIDE | 2011 |
|
RU2455280C1 |
METHOD OF OBTAINING N-PHENYL-ADAMANTANE-1-CARBOXAMIDE DERIVATIVES | 2016 |
|
RU2626237C1 |
METHOD OF SYNTHESIS OF 1-CHLOROADAMANTANE, 1- AND 4-CHLORODIAMANTANES | 2000 |
|
RU2185364C1 |
Authors
Dates
2011-11-27—Published
2009-11-30—Filed