Acetic Anhydride → 5-Acetamido-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole

HRID 1462131Notes

Reaction equation

HRID 1462131 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[C:8]=2[Cl:15])[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[C:18](OC(=O)C)(=[O:20])[CH3:19]>>[C:18]([NH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[C:8]=2[Cl:15])[N:5]=[CH:4][C:3]=1[C:16]#[N:17])(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 30189015-amino-1-(2,3,4-trichlorophenyl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 131275295-Acetamido-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole

Procedure

5-Amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole (28.7 g) was heated at reflux in acetic anhydride (150 ml) for 8 hours. The reaction mixture was then evaporated to dryness and the solid residue was suspended in ethanol (250 ml). Saturated aqueous sodium bicarbonate solution was then added to give a pH of 8 and the suspension was then stirred magnetically for 16 hours. The solid obtained was separated by filtration, washed with water and dried, to give 5-acetamido-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole (23.7 g), m.p. 222°-224° C., in the form of an off-white powder.

Workup

  1. customThe reaction mixture was then evaporated to dryness
  2. additionSaturated aqueous sodium bicarbonate solution was then added
  3. customto give a pH of 8
  4. customThe solid obtained
  5. customwas separated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-af57e9d0a4d44b9b868bb5f1c60f759a
Source dataset
uspto-grants-1984_07
Patent number
US04459150

Reaction notes

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