Thiourea → HCID 178527908, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-chloro-1H-1,3-azaphospholo[4,5-d]pyrimidine (compound 14, 0.23 g, 1.33 mmol), thiourea (0.15 g, 2.0 mmol) and absolute ethanol (10 mL) was heated under reflux for 90 min with stirring under anhydrous conditions. The reaction mixture was cooled to 25° C. and then the solvent was evaporated in vacuo. The residue was sonicated with ice-cold water (10 mL) and the precipitate was collected by filtration, washed with cold water (3×5 mL) and dried over P2O5 in vacuo first at 25° C. and then at 100° C. to yield 0.12 g (55%) of the title compound, mp>300° C. Ir (KBr): ν710 (=P-C), 1170 and 1200 (-P=CH), 1580 (C=S), and 3280 (NH) cm-1. Uv (MeOH): λmax230 nm (ε19,400), 276 (9400), and 338 (17,200). 1H nmr (DMSO-d6): 8.11 (s, 1 H, C5H), 8.93 (dd, 1 H, JC2H,NH =5.4 Hz, JC2H,P =39.6 Hz, C2H), δ 13.15 (s, 1 H, NH), and 13.82 (s, 1 H, NH). Anal. Calcd. for C5H4N3PS.H2O: C, 32.08; H, 3.23; N, 22.45; S, 17.13. Found: C, 32.39; H, 3.61; N, 22.54; S, 17.40. ##STR11##

Provenance & Evidence