Acetic Anhydride → HCID 20453877, compound

HRID 1462136Notes

Reaction equation

HRID 1462136 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[C:9]([Cl:18])[C:8]=2[Cl:19])[N:5]=[CH:4][C:3]=1[C:20]#[N:21].[C:22](OC(=O)C)(=[O:24])[CH3:23]>O>[C:22]([NH:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:15])[F:16])=[C:9]([Cl:18])[C:8]=2[Cl:19])[N:5]=[CH:4][C:3]=1[C:20]#[N:21])(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13122001HCID 13122001, compound

Product 1

HCID 20453877HCID 20453877, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Amino-4-cyano-1-(2,3,6-trichloro-4-trifluoromethylphenyl)pyrazole (3.74 g) in acetic anhydride (20 ml) was heated at reflux for 6 hours. The reaction mixture was then evaporated under reduced pressure to remove unreacted acetic anhydride. The residual oil was dissolved in dichloromethane (50 ml) and filtered. The filtrate was evaporated to give a foam, which was then suspended in water (70 ml). The suspension was filtered and the filtrate deposited a solid on standing. The solid was collected by filtration and washed with water to give 5-acetamido-4-cyano-1-(2,3,6-trichloro-4-trifluoromethylphenyl)pyrazole (0.4 g), m.p. 177°-178° C., in the form of a fawn-coloured solid.

Workup

  1. temperatureat reflux for 6 hours
  2. customThe reaction mixture was then evaporated under reduced pressure
  3. customto remove unreacted acetic anhydride
  4. dissolutionThe residual oil was dissolved in dichloromethane (50 ml)
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. customto give a foam, which
  8. filtrationThe suspension was filtered
  9. filtrationThe solid was collected by filtration
  10. washwashed with water

Sources & evidence

ORD record
ord-0fbe4585ccd74e27bdad730164787c32
Source dataset
uspto-grants-1984_07
Patent number
US04459150

Reaction notes

Loading…