1088. The action of sulphur monochloride on amides of monocarboxylic acids

Abstract

Monocarboxylic acid amides frequently give monosulphides, (RCO*NH)2S, with sulphur monochloride. Diacyl hydrazides, (RCOoNH) 2, are not formed as was previously supposed. Formamide gives an adduct containing nitrogen but no sulphur. The evolution of hydrogen chloride from the reaction with benzamide shows first-order kinetics in its early stages.THE reaction of sulphur monochloride, S2C12, with carboxyamides has been studied by Naik,l and by Naik and Patel.2 The products described were :(i) monosulphides, (RKOoNH) $5, from acetamide, monochloroacetamide , n-butyr-(ii) a disulphide, (NCOCH=CO.NH~)~S~, from cyanoacetamide, (iii) diacyl hydrazides, (R*CO*NH)2, from trichloroacetamide , isobutyramide , n-valer-

3,4-Disubstituted and fused 1,2,5-thiadiazole n-oxides

“…For example, benzofurazan N,N-dioxide (20) has been shown to be unstable with respect to ring opening.25 Another plausible explanation may be that the hypothetical B is easily reduced by any S+1 or S+2 source present in the reaction mixture before and after hydrolysis. The high oxidiz-20 21, Jodinin (R = H) 22, Myxin (R = CH3) ing power of phenazine , -dioxides, such as the broadspectrum antibiotics Jodinin6 (21) and Myxin26,27 (22), we regard as additional supporting evidence for path a.…”

General synthetic system for 1,2,5-thiadiazoles

“…Caled for C2HC1N2S: C, 19.92; , 0.84; Cl, 29.41;N,23.24;8,26.60. Found: C,20.12; , 0.84; Cl,29.39;N,23.31;8,26.87. B. From 3-Hydroxy-l,2,5-thiadiazole.-A mixture of 2.06 g (0.02 mole) of 3-hydroxy-l,2,5-thiadiazole and 4.0 ml of phosphorus oxychloride was heated at 80°in an open Carius tube until the evolution of hydrogen chloride ceased (about 0.5 hr).…”

Reactions of Phthalimide and Potassium Phthalimide With Sulfur Monochloride

“…The reaction of ainines and amides with sulfur monochloride (S2CI2) in a variety of nonpolar solvents and in absolute ethanol has been reported to j~ield mixtures of N,N'-dithio and N,N'-polythio compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11). In a few instances, substances identified as N,N'-monothio derivatives of anlines and amides have been isolated (2,3,12,13).…”