Process for the manufacture of 5- mercapto-1,2,3-triazoles

Details Process for the manufacture of 5- mercapto-1,2,3-triazoles Process for the manufacture of 5- mercapto-1,2,3-triazoles

C - Chemistry, Metallurgy

07

D

260/313

C07D 249/04 (2006.01) C07D 285/06 (2006.01)

Patent

CA 1143739

ABSTRACT The present invention provides a process for the preparation of a compound of the general formula Image I in which R1 represents a hydrogen atom or an unsubstituted or substituted (C1-C4)-alkyl radical, or an alkali metal or alkaline earth metal salt thereof, which comprises (a) reacting a compound of the general formula Image II with a compound of the general formula Image III, when R2 represents a hydrogen atom, in the presence of an acid-binding agent, to form a compound of the general formula Image IV, (b) reacting this with a compound of the general formula H-O-R4 V, to form a compound of the general formula Image VI, (c) reacting this in an acid-catalysed or base-catalysed reaction to form a compound of the general formula Image VII, and (d) transposing this in the presence of a base, and, if desired, liberating the compound of the general formula I from the reaction product, wherein R2 represents a hydrogen atom or the monovalent equivalent of a metal, R3 represents an unsubstituted or substituted alkylcarbonyl radical having 1 to 4 carbon atoms in the alkyl moiety, an alkoxycarbonyl radical having 1 to 4 carbon atoms in the alkoxy moiety, an unsubstituted or substituted benzoyl radical, an unsubstituted or substituted aryl- sulphonyl radical or an unsubstituted or substituted alkylsulphonyl radical, R4 represents an unsubstituted or substituted (C1-C4)-alkyl radical, an unsubstituted or substituted (C5-C8)-cyclo- alkyl radical, an unsubstituted or substituted aryl- (C1-C3)-alkyl radical or an aromatic hydrocarbon radical unsubstituted or substituted by one or more of the same or different substituents selected from (C1-C6)-alkyl radicals, halogen atoms, (C1-C6)-alkoxy radicals, nitro groups, and trifluoromethyl groups, and X represents a halogen atom, and R1 has the meaning given above. By this process 5-mercapto-1,2,3-triazoles, which are impor- tant as starting materials for the manufacture of plant- protecting agents and medicaments can be manufactured with- out isolation of intermediates that are harmful from the safety point of view. Moreover, crude compounds of the general formula II, which can be pre- pared from readily available starting materials, can be used.

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