Verfahren zur Herstellung von Dihydro-1, 3, 5-dithiazinverbindungen

摘要

Dithiazine compounds of the general formula: in which R is an alkyl, aryl, alkaryl, aralkyl, alicyclic or heterocyclic radical which may contain one or more hydroxyl, hydroxyalkyl, carboxyl or sulphydryl groups, are prepared by reacting formaldehyde or a substance yielding formaldehyde, a primary amine of the formula RNH2 and hydrogen sulphide in alkaline solution or an alkali metal hydrogen sulphide. In a modification of the process compounds of the general formula: are obtained by reacting a diamine of formula H2N-R1-NH2 in which R1 is an alkylene radical or a divalent alkaryl, aralkyl, aryl, cycloalkyl or heterocyclic radical with formaldehyde or substances yielding formaldehyde and hydrogen sulphide or an alkali metal hydrogen sulphide in alkaline solution. Suitable amines for use as starting materials are, for example, methylamine, ethylamine, isopropylamine, ethanolamine, propanolamine, glycine, alanine, serine, glutamic acid asparagine, b -alanine, g -aminobutyric acid, e -aminocaproid acid, 11-aminoundecanoic acid, p-aminophenol, o-aminobenzoic acid and ethylene diamine. Instead of formaldehyde, oligoners of formaldehyde, for example paraformaldehyde, may be used. The reaction is preferably carried out in the presence of a solvent, for example water, a C1-C8 aqueous alcohol, or an alcohol. Examples are given of the preparation of (a) N-methyl-dihydro-1,3,5-dithiazine; (b) dihydro-1, 3, 5-dithiazinyl acetic acid; (c) a -dihydro-1,3,5-dithazinyl propionic acid; (d) b -dihydro-1,3,5-dithiazinyl propionic acid; (e) 1,2 bis-(dihydro-11,31,51-dithiazinyl)-ethane; (e) dithiazinyl ethanol; (f) the compound of formula: (g) the compound: (h) the compound: (j) the compound: and (k) the compound: