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

HRID 1392347

Reaktionsgleichung

Reaktionsgleichung von HRID 1392347
[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

Komponenten

4

Edukt 2

HCID 6145PhenylureaHCID 75990(Chlorothio)formyl chloride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6ea1f06e69b14bb7a35424f1d7961e08
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342037B2

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