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

HRID 1270557

Reaction equation

HRID 1270557 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, 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).

Workup

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

Sources & evidence

ORD record
ord-64e0cb0f60d3469799b062732197bd1b
Source dataset
uspto-grants-2007_04
Patent number
US07202257B2

Linked notes

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