Sulfuric Acid → [3-(4-Chlorobenzoyl)-1,2,4-oxadiazol-5-yl]acetamide

HRID 638564Notes

Reaction equation

HRID 638564 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[N:12]=[C:11]([CH2:13][C:14]#[N:15])[O:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH:18]S(O)(=O)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]=[C:11]([CH2:13][C:14]([NH2:15])=[O:18])[O:10][N:9]=2)=[O:7])=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 13576490[3-(4-Chlorobenzoyl)-1,2,4-oxadiazol-5-yl]acetonitrile

Product 1

HCID 13576495[3-(4-Chlorobenzoyl)-1,2,4-oxadiazol-5-yl]acetamide

Procedure

A mixture of 2.8 g of [3-(4-chlorobenzoyl)-1,2,4-oxadiazol-5-yl]acetonitrile and 25 ml of 98% H2SO4 was stirred at room temperature overnight. The resulting solution was added slowly to 500 ml of ice water with mechanical stirring to precipitate a solid. The collected solid was washed with excess water and dried in vacuo to give 2.6 g of a solid. Recrystallization from isopropanol yielded 2.12 g (71%) of crystals, m.p. 156°-158°.

Workup

  1. stirringwith mechanical stirring
  2. customto precipitate a solid
  3. washThe collected solid was washed with excess water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-085a5808b4f44499940161dc259631c2
Source dataset
uspto-grants-1985_12
Patent number
US04562186

Reaction notes

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