4-Cyano-5-diacetylamino-1-(2,3,4-trichlorophenyl)pyrazole → 5-Acetamido-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole

HRID 1462132Notes

Reaction equation

HRID 1462132 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[C:16]=2[Cl:23])[C:7]=1[N:8](C(=O)C)[C:9](=[O:11])[CH3:10])#[N:2]>C(O)C.C(=O)(O)[O-].[Na+]>[C:9]([NH:8][C:7]1[N:6]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[C:16]=2[Cl:23])[N:5]=[CH:4][C:3]=1[C:1]#[N:2])(=[O:11])[CH3:10]

Participants

4

Reactant 1

HCID 131275314-Cyano-5-diacetylamino-1-(2,3,4-trichlorophenyl)pyrazole

Product 1

HCID 131275295-Acetamido-4-cyano-1-(2,3,4-trichlorophenyl)pyrazoleYield 50.7%

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateCatalystHCID 702EthanolSolvent

Procedure

4-Cyano-5-diacetylamino-1-(2,3,4-trichlorophenyl)pyrazole (0.2 g) in ethanol (5 ml) containing saturated aqueous sodium bicarbonate solution (4 drops), was heated at reflux for 20 minutes. The reaction mixture was then evaporated to dryness under reduced pressure (20 mmHg) to give a fawn coloured powder which was crystallized from ethanol (2 ml), to give 5-acetamido-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole (0.09 g), m.p. 222°-224° C., in the form of a colourless crystalline solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 minutes
  3. customThe reaction mixture was then evaporated to dryness under reduced pressure (20 mmHg)
  4. customto give a fawn
  5. customwas crystallized from ethanol (2 ml)

Sources & evidence

ORD record
ord-6c1afaf64ad2495db27f59294506964c
Source dataset
uspto-grants-1984_07
Patent number
US04459150

Reaction notes

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