Phenylurea → 2-Phenyl-1,2,4-thiadiazolidine-3,5-dione

Participants

Reaction Steps

To the solution of phenyl-urea (13.0 g, 95.48 mol) in THF (100 mL) was slowly added chlorocarbonyl sulfenylchloride (13 mL, 148.85 mmol) at RT. The reaction mixture was refluxed overnight, the volatiles removed in vacuo yielded 2-phenyl-1,2,4-thiadiazolidine-3,5-dione as a white solid (4.0 g, 20%). 1H NMR (DMSO-d6): δ 12.49 (s, 1H), 7.51 (d, J=8.0 Hz, 2H), 7.43 )t, J=7.6 Hz, 2H), 7.27 (t, J=7.2 Hz, 1H).

Provenance & Evidence