Acetic Anhydride → N-(5-methyl-1H-pyrazol-3-yl)acetamide

HRID 1953802Notes

Reaction equation

HRID 1953802 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][C:7]1[CH:11]=[C:10]([CH3:12])[NH:9][N:8]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>O>[C:13]([NH:6][C:7]1[CH:11]=[C:10]([CH3:12])[NH:9][N:8]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 5246311N-(5-methyl-1H-pyrazol-3-yl)acetamideYield 59.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50.4 g (0.6 mol) of sodium bicarbonate were added in small amounts at room temperature to a solution of 19.4 g (0.2 mol) of 3-amino-5-methyl-1H-pyrazole in 200 cm3 of water. 37.8 cm3 (0.4 mol) of acetic anhydride were added dropwise to this solution and then the mixture was heated at reflux for 2 hours. The solution was subsequently brought back to room temperature, a white solid crystallized and was pulled dry on sintered glass and then washed with 100 cm3 of water. After drying under vacuum at 40° C., 16.6 g of the expected product were obtained in the form of pearlescent-white crystals, the melting point of which was between 210° C. and 212° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customwas subsequently brought back to room temperature
  4. customa white solid crystallized
  5. customwas pulled dry on sintered glass
  6. washwashed with 100 cm3 of water
  7. customAfter drying under vacuum at 40° C.

Sources & evidence

ORD record
ord-e6217960ed134687af208f44f197710d
Source dataset
uspto-grants-2000_09
Patent number
US06118008

Reaction notes

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