Patent GB607765
Carboxylic amides are prepared by heating acyclically unsaturated compounds with sulphur and basic trivalent nitrogen compounds which have hydrogen attached to the nitrogen. The unsaturated compound may contain an olefinic or acetylenic linkage and may be a hydrocarbon or may also contain groups such as the ether, ester, ketone, aldehyde, amide, carboxylic acid or alcohol group, and examples are given of many such compounds and also of suitable nitrogen compounds. The reaction may be carried out in an aqueous or organic solvent. The sulphur may be used in the reaction mixture as flowers of sulphur or may be dissolved in the nitrogen base as a polysulphide. Examples are given of the production of (1) phenylacetamide from styrene, aqueous ammonia and sulphur in pyridine; (2) phenylacetamide from phenylacetylene, sulphur and aqueous ammonia in pyridine; (3) phenylacetamide from phenylacetylene and ammonium sulphide-sulphur in dioxane; (4) phenylacetamide from styrene and ammonium sulphide-sulphur in dioxane; (5) phenylacetothiomorpholide from styrene, sulphur and morpholine; (6) phenylacetothiomorpholide from phenylacetylene, sulphur and morpholine; (7) b -phenylpropionamide from 1-phenylpropene-1, sulphur and ammonium sulphide solution in pyridine; (
b -phenylpropionamide from 1-phenylpropene-1, sulphur and aqueous ammonia in pyridine; (9) b -phenylpropionamide from 1-methyl-2-phenylacetylene, ammonium sulphide solution and sulphur in pyridine; (10) n-heptamide from 1-heptene, ammonium sulphide solution and sulphur in pyridine; (11) n-heptamide from 1-heptene, aqueous ammonia and sulphur in pyridine; (12) a -phenylpropionamide from a -methylstyrene, aqueous ammonia and sulphur in pyridine; (13) 2-naphthylacetothiomorpholide from 2-naphthylethylene, sulphur and morpholine and b -(2,4 - dichlorophenoxy) - propiothiomorpholide from 2,4-dichlorophenylallyl ether, sulphur and morpholine-the former may be converted to the corresponding carboxylic acid by hydrolysis in presence of acetic and hydrochloric acids-and (14) 2-pyridylacetamide from 2-vinylpyridine, sulphur and aqueous ammonia in pyridine.