Diazomethane → N-(1,2,3-Thiadiazol-5-yl)benzamide

HRID 268131Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 268131
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:12](=[CH2:14])=[N-:13]>CCOCC>[C:1]([NH:9][C:10]1[S:11][N:13]=[N:12][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 9550DiazomethaneHCID 68284Benzoyl isothiocyanate

Produkt 1

HCID 319747N-(1,2,3-Thiadiazol-5-yl)benzamideAusbeute 36,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a stirred solution of benzoylisothiocyanate (50.6 g., 310 mmoles) in commercial anhydrous ether (400 ml.), maintained at 0° and in a nitrogen atmosphere, was added dropwise with vigorous stirring, 0.685 N ethereal diazomethane (453 ml., 310 mmoles). When the addition was completed, the mixture was stirred for 1 hour at 0°, the solid was collected by filtration and dried in vacuo. The melting point of the crude material (23.3 g.) thus obtained was observed somewhere in the region 232° to 257°. Goerdler reported M.p. 267° for the pure material. A small second crop (2.1 g.) was obtained by evaporation of the mother liquor in vacuo. The total yield was therefore 40%.

Aufarbeitung

  1. additionWhen the addition
  2. filtrationthe solid was collected by filtration
  3. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-11587bd8483a4699b52af6e688f52bb3
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03946000

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