Acetic Anhydride → 4-Acetylaminopyrazole

HRID 64063Notes

Reaction equation

HRID 64063 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH:8]1[CH:12]=[C:11]([NH2:13])[CH:10]=[N:9]1>>[NH:8]1[CH:12]=[C:11]([NH:13][C:5](=[O:7])[CH3:6])[CH:10]=[N:9]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 780351H-pyrazol-4-amine

Product 1

HCID 123468944-AcetylaminopyrazoleYield 54%

Procedure

Acetic anhydride (0.7 ml, 8.433 mmol) was added dropwise at 0° C. to 1H-pyrazol-4-amine (0.7 g, 8.433 mmol). The mixture was stirred for 30 min at RT and quenched by the addition of crushed ice. The mixture was extracted with ethyl acetate The combined organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to afford the product in 54% yield. (0.6 g). LC-MS (ESI): Calculated mass: 125.0; Observed mass 126.0 [M+H]+ (rt: 0.115 min).

Workup

  1. customquenched by the addition of crushed ice
  2. extractionThe mixture was extracted with ethyl acetate The combined organic layer
  3. washwas washed with water, brine
  4. dry with materialdried over sodium sulphate
  5. distillationThe solvent was distilled off
  6. customto afford the product in 54% yield
  7. customObserved mass 126.0 [M+H]+ (rt: 0.115 min)

Sources & evidence

ORD record
ord-8ab6f322a46a421fbe42a35777ecd14b
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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