Process for the preparation of 2-mercaptoalkyl-sulphides and 2-mercaptoalkylethers

Claim 2

A process for the preparation of a compound of the following structural formula R--X--Et--SH (I) by treating a compound of the following structural formula ##STR19## with a compound of the following structural formula ##STR20## in which R represents an organic radical comprising at least one alkyl, aralkyl or aryl group which may be substituted and which may be interrupted by S- and/or O-atoms, X represents an oxygen atom or a sulphur atom, Et represents an ethylene group which may be substituted and which may form part of a 5- or 6-membered ring system, R 10 to R 13 which may be the same or different, represent H; an alkyl group having from 1-6 C-atoms which may be substituted or an aryl radical which may be substituted and/or at least one pair of the substituents R 10 to R 13 may represent the atoms required to complete a heterocyclic 5- or 6-membered ring, R 20 to R 22 which may be the same or different, represent hydrogen, an alkyl group having from 1-5 C-atoms or aryl radical which may be substituted or R 20 together with R 21 represent the atoms required to complete a ring, A represents an anion which may be multivalent.

Claim 3

A process according to claim 1, wherein the the reaction takes place between 0° and 120° C. at pH 6 to 12.

Claim 4

A process for the preparation of a compound of a structure according to formula Ia or Ib: ##STR21## in which: R 1 represents an aliphatic radical having from 2 to 20 carbon atoms, which may be substituted by aryl or interrupted by phenylene, or by O or S atoms, or an alicyclic radical, having from 5 to 7 carbon atoms, or phenyl, chlorophenyl, o-carboxy phenyl, benzyl, and said R 1 radical may be substituted with a mercapto group; R 2 , R 3 , R 4 and R 5 which may be the same or different represent hydrogen; an alkyl group, having from 1 to 6 carbon atoms which may be substituted; phenyl, and/or at least one pair from the group R 2 to R 5 represents the atoms required to complete a 5- or 6-membered ring; X represents an oxygen atom or a sulphur atom; R 6 represents H or: an aliphatic radical having 2 to 10 aliphatically bound carbon atoms, which may be substituted by aryl or cycloalkyl or interrupted by arylene or a radical derived from a polyalkylene oxide having from 4 to 20 carbon atoms interrupted by ether groups, a phenyl or phenylene groups, which may be interrupted by alkylene groups, an alicyclic radical, having from 5 to 7 carbon atoms, or benzyl or phenethyl; the R 6 group may be interrupted by at least one oxygen and/or sulphur atom, m represents an integer from 1 to 100; n represents an integer from 1 to 4; o represents an integer from 1 to 3; p represents an integer of from 2 to 20; B represents H or --CO--R 8 ; and R 8 represents --NH-alkyl; --NH-aryl; --O-alkyl; alkyl or carboxy-alkyl, and said R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 8 radicals and groups may be substituted with carboxyl, carbonamide-, acetylamino- sulphonamino-, ureido- and ester groups, by reacting the S-alkyl- isothiuronium salt of compound Ia or Ib with a hydrazine of the following structural formula ##STR22## in which R 20 to R 22 may be the same or different, represent hydrogen, an alkyl group having from 1-5 C-atoms or aryl radical which may be substituted or R 20 together with R 21 represent the atoms required to complete a ring.

Claim 5

A process for the preparation of a compound of a structure according to formula Ia or Ib: ##STR21## in which: R 1 represents an aliphatic radical having from 2 to 20 carbon atoms, which may be substituted by aryl or interrupted by phenylene, or by O or S atoms, or an alicyclic radical, having from 5 to 7 carbon atoms, or phenyl, chlorophenyl, o-carboxy phenyl, benzyl, and said R 1 radical may be substituted with a mercapto group; R 2 , R 3 , R 4 and R 5 which may be the same or different represent hydrogen; an alkyl group, having from 1 to 6 carbon atoms which may be substituted; phenyl, and/or at least one pair from the group R 2 to R 5 represents the atoms required to complete a 5- or 6-membered ring; X represents an oxygen atom or a sulphur atom; R 6 represents H or: an aliphatic radical having 2 to 10 aliphatically bound carbon atoms, which may be substituted by aryl or cycloalkyl or interrupted by arylene or a radical derived from a polyalkylene oxide having from 4 to 20 carbon atoms interrupted by ether groups, a phenyl or phenylene groups, which may be interrupted by alkylene groups, an alicyclic radical, having from 5 to 7 carbon atoms, or benzyl or phenethyl; the R 6 group may be interrupted by at least one oxygen and/or sulphur atom, m represents an integer from 1 to 100; n represents an integer from 1 to 4; o represents an integer from 1 to 3; p represents an integer of from 2 to 20; B represents H or --CO--R 8 ; and R 8 represents --NH-alkyl; --NH-aryl; --O-alkyl; alkyl or carboxy-alkyl, and said R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 8 radicals and groups may be substituted with carboxyl, carbonamide-, acetylamino- sulphonamino-, ureido- and ester groups, by reacting the S-alkyl- isothiuronium salt of compound Ia or Ib with a hydrazine of the following structural formula ##STR22## in which R 20 to R 22 may be the same or different, represent hydrogen, an alkyl group having from 1-5 C-atoms or aryl radical which may be substituted or R 20 together with R 21 represent the atoms required to complete a ring.

Claim 6

A process according to claim 3, wherein R 1 represents alkyl having from 2 to 20 carbon atoms; phenyl or benzyl, R 2 to R 5 represent H; alkyl having from 1 to 6 carbon atoms; phenyl and/or at least one pair from the substitutents R 2 to R 5 represent the atoms required to complete a cyclopentyl or cyclohexyl ring, x represents oxygen or sulphur, R 6 represents alkyl having 2 to 10 carbon atoms; phenyl, benzyl or phenethyl; m represents an integer from 1 to 100; n represents an integer from 1 to 4; o represents an integer from 1 to 3; p represents an integer from 2 to 20 and B represents hydrogen.

Claim 7

A process according to claim 4, wherein R 1 represents --CH 2 --CHR 7 --SH, and R 7 represents H, CH 3 or C 2 H 5 .

Claim 8

A process as claimed in claim 3 wherein the hydrazine is selected from the group consisting of phenyl hydrazine; N,N-dimethylhydrazine, N-aminomorpholine and their salts and hydrates.