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

HRID 492035

Reaction equation

HRID 492035 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-759bce7b25b84c5180437af1d44f6f5c
Source dataset
uspto-grants-2009_05
Patent number
US07531566B2

Linked notes

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