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

HRID 1180111

Reaktionsgleichung

Reaktionsgleichung von HRID 1180111
[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, 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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-902e972584234075977090351cfc6e11
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279576B2

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