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

HRID 1392347Notes

Reaction equation

HRID 1392347 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, 1 H).

Workup

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

Sources & evidence

ORD record
ord-6ea1f06e69b14bb7a35424f1d7961e08
Source dataset
uspto-grants-2008_03
Patent number
US07342037B2

Reaction notes

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