Acetic Anhydride → HCID 13127532, compound

HRID 1462134Notes

Reaction equation

HRID 1462134 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([F:13])=[C:11]([F:14])[C:10]([C:15]([F:18])([F:17])[F:16])=[C:9]([F:19])[C:8]=2[F:20])[N:5]=[CH:4][C:3]=1[C:21]#[N:22].[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:23]([NH:1][C:2]1[N:6]([C:7]2[C:12]([F:13])=[C:11]([F:14])[C:10]([C:15]([F:18])([F:17])[F:16])=[C:9]([F:19])[C:8]=2[F:20])[N:5]=[CH:4][C:3]=1[C:21]#[N:22])(=[O:25])[CH3:24]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 13121999HCID 13121999, compound

Product 1

HCID 13127532HCID 13127532, compound

Procedure

5-Amino-4-cyano-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole (6.5 g) in acetic anhydride (30 ml) was heated at reflux for 3.5 hours. The reaction mixture was then evaporated to dryness and the solid residue was dissolved in ethanol (50 ml). Saturated aqueous sodium bicarbonate solution was then added to give a pH of 7-8 and the solution was then evaporated to dryness. The solid residue was triturated with hexane (20 ml) to give an off-white powder which was crystallized from toluene (50 ml) to give 5-acetamido-4-cyano-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole (1.4 g), m.p. 153°-154° C., in the form of colourless crystals.

Workup

  1. temperatureat reflux for 3.5 hours
  2. customThe reaction mixture was then evaporated to dryness
  3. dissolutionthe solid residue was dissolved in ethanol (50 ml)
  4. additionSaturated aqueous sodium bicarbonate solution was then added
  5. customto give a pH of 7-8
  6. customthe solution was then evaporated to dryness
  7. customThe solid residue was triturated with hexane (20 ml)
  8. customto give an off-white powder which
  9. customwas crystallized from toluene (50 ml)

Sources & evidence

ORD record
ord-ce9c131f7ed047b7ba14133a12686c3a
Source dataset
uspto-grants-1984_07
Patent number
US04459150

Reaction notes

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