Mameli, Efisio published the artcileAminolysis of ethylxanthogenamide. III, Quality Control of 14294-10-1, the publication is Annali di Chimica (Rome, Italy) (1956), 545-62, database is CAplus.
cf. C.A. 51, 3458d. EtOCSNH2 (I) reacts with 2 moles RNH2 at room temperature to give RNHCSNH2 (II); the rate of reaction and yield are greatly increased by addition of 0.3 mole KOH. Yields of II obtained without and with KOH, resp., are: from MeNH2, 61, 79; EtNH2, 57, 61; PrNH2, 39, 79; iso-PrNH2, 42, 45; BuNH2, 22, 71; PhCH2NH2, about 16, 61; cyclohexylamine, 12, 36. Reaction times are up to 50 days. No byproducts (except SCN–) are found when KOH is used; the following are detected in experiments without KOH: (MeNH)2C:NH, (EtNH)2C:NH, BuNHCSOEt, [(PhCH2NH)2C:NH]2.H2S2O3 (III), C6H11NHCSOEt. Reaction between 2.1 g. I and 2 moles 33% aqueous PhCH2NH2 in 6 cc. EtOH gives first a precipitate of II, then (after exposure of the filtrate to air) an oil, from which III is obtained by crystallization from Me2CO. III, m. 168-9°, is identified by conversion to (PhCH2NH)2C:NH and its hydrochloride; its infrared spectrum is given. Me2NH reacts with I in aqueous EtOH to give 7% Me2NCSOEt and 10% [Me2NC(:NH)NH2]2.H2S2O3, but in the presence of KOH gives 67% Me2NCSNH2. Et2NH and iso-Bu2NH fail to react. Pyrrolidine after 4 days with I in aqueous EtOH gives 30% 1-(thiocarbamyl)pyrrolidine, m. 193-7° (dependent on the rate of heating), which isomerizes to the corresponding thiocyanate above the m.p.; the same product (84%) is obtained in 1 day when KOH is added. Piperidine and I without KOH give only traces of 1-(thiocarbethoxy)piperidine and 1-(thiocarbamyl)piperidine; with KOH 27% of the latter is formed. Piperidine, I, and 1 mole 30% NH3 in aqueous solution evaporated after 30 days give 7% 1-guanylpiperidine hyposulfite, m. 246-7° (variable). Morpholine gives approx. 20% N-(ethoxythiocarbonyl)morpholine and 15% N-guanylmorpholine hyposulfite, m. 263-5° (variable); addition of 1 mole NH3 increases these yields to about 30% each, but addition of 0.3 mole KOH changes the reaction completely, the only product being N-(thiocarbamyl)morpholine (50%). In general, increase in KOH concentration or temperature only leads to increased decomposition of I. Attempts to make I react with (HOCH2CH2)2NH or with aromatic amines at room temperature or above were unsuccessful. Formation of hyposulfites is ascribed to spontaneous oxidation of S—, but yields are not improved by aeration or addition of H2O2. The variety of products obtained from I is ascribed to the possibility of tautomerism.
Annali di Chimica (Rome, Italy) published new progress about 14294-10-1. 14294-10-1 belongs to amides-buliding-blocks, auxiliary class Morpholine,Thiourea,Amine,Amide, name is Morpholine-4-carbothioamide, and the molecular formula is C5H10N2OS, Quality Control of 14294-10-1.
Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics