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

HRID 1180111Notes

Reaction equation

HRID 1180111 reaction equation
[C:1]1([NH:7][C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:12]([S:14]Cl)=[O:13]>C1COCC1>[C:1]1([N:7]2[C:8](=[O:9])[NH:10][C:12](=[O:13])[S:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6145PhenylureaHCID 75990(Chlorothio)formyl chloride

Product 1

HCID 184498842-Phenyl-1,2,4-thiadiazolidine-3,5-dioneYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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, yield 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, 1 H).

Workup

  1. customat RT
  2. temperatureThe reaction mixture was refluxed overnight
  3. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-902e972584234075977090351cfc6e11
Source dataset
uspto-grants-2007_10
Patent number
US07279576B2

Reaction notes

Loading…