2-AMINO-2-THIAZOLINE .6. FORMATION OF A THIAZOLO-S-TRIAZINE FROM 2-AMINO-2-THIAZOLINE

The reaction of 2-amino-2-thiazoline (I) with excess phenylisothiocyanate in acetonitrile solution gives hydrogen sulfide, 1-phenyl-3-(2-thiazolin-2-yl)-2-thiourea (II) and a compound, C17H14N4S2 (III). Hydrolysis of III with cone HCl gave 1-(2-mercaptoethyl)-3-phenyl-2,4,6-trioxohexahydro-s-triazine (IV), aniline hydrochloride and hydrogen sulfide. Dilute hydrochloric acid hydrolysis of III gave one product, 1-(2-mercaptoethyl)-3-phenyl-4-phenylimino-2-thioxo-6-oxohexahydro-s-triazine (VIa). This compound was oxidized to the corresponding disulfide (VII) whose thiocarbonyl group was then replaced by a carbonyl group to give VIII. By comparison of the NMR spectra of the degradation products of III it was possible to assign to it the structure, 2-phenylimino-3-phenyl-4-thioxothiazolo[3.2-a]tetrahydro-s-triazine (IIIa). © 1969.