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

HRID 596764Notes

Reaction equation

HRID 596764 reaction equation
[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

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 68284Benzoyl isothiocyanate

Product 1

HCID 319747N-(1,2,3-Thiadiazol-5-yl)benzamideYield 36.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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%.

Workup

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

Sources & evidence

ORD record
ord-7cc5b7a7986c44139cc5f8a954b3b532
Source dataset
uspto-grants-1977_03
Patent number
US04012382

Reaction notes

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