Nair, G. Vijayakumaran published the artcileTert-butyl and tert-amyl isothiocyanates as novel reagents for the preparation of 1-substituted thiocarbamide derivatives, Recommanded Product: Morpholine-4-carbothioamide, the publication is Indian Journal of Chemistry (1966), 4(12), 516-20, database is CAplus.
cf. Neville and McGee, CA 59: 8715f. tert-Butyl (I) and tert-amyl isothiocyanates (II) on treating with amino compounds, aliphatic and aromatic primary and secondary amines, heterocyclic primary amines and imines and cyclic amines, in which the amino group is part of the ring system, afforded the related tertiary alkyl thiocarbamide derivatives [TABLE OMITTED] I was prepared as follows: A mixture of 27.4 g. NH4CNS, 10 g. ZnCl2, 27.8 g. tert-BuCl, and 100 ml. H2O was shaken 96 hrs. at intervals. The upper organic layer was separated, washed with H2O, dried and shaken 1 hr. with 5 g. powd. anhydrous ZnCl2 for 96 hrs. The decanted liquid was washed with H2O and dried with CaCl2 to yield 29.5 g. I, which was used directly for condensation. II was similarly prepared using tert-AmCl. Molar quantities of aliphatic primary and secondary amines and I reacted rapidly at room temperature in petroleum ether solution giving quant. yields of the desired tertiary alkyl thiocarbamide derivatives Aromatic primary and secondary amines, heterocyclic amines, and mono- and diarylguanidines, however, reacted only when the reactants were heated 1.5-5 hrs. in C6H6 solution II also reacted similarly. These derivatives were easily and quant. heterolyzed by treating with concentrated HCl at 90-95° for 2-30 min. to the corresponding thiocarbamides and tertiary alkyl chloride. 1-Substituted-3-tert-butylthiocarbamides (III) prepared are listed in the first table. 1-Substituted-3-tert-amylthiocarbamides (IV) prepared by the reaction of II and amines are listed in the 2nd table. (Ts stands for thiosemicarbazide). [TABLE OMITTED] The reaction of I with N2H4.H2O for 30 min. yielded 90% 4-tert-butylthiosemicarbazide (V), m. 143° (dilute EtOH). Similar reaction with PhNHNH2 yielded 91% 2-phenyl-4-tert-butylthiosemicarbazide (VI), m. 177° (absolute EtOH). Heterolysis of V and VI yielded H2NNHCSNH2, m. 180°, and PhNHNHCSNH2, m. 201°, in 67 and 94% resp. This procedure provides a novel and economic method of wider applicability for the preparation of 1-substituted thiocarbamides.
Indian Journal of Chemistry 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, Recommanded Product: Morpholine-4-carbothioamide.
Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics