Acetyl chloride → N-(1,3,5-trimethylpyrazol-4-yl)acetamide

HRID 2119803Notes

Reaction equation

HRID 2119803 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[N:4][N:5]([CH3:8])[C:6]=1[CH3:7].C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18]>>[C:17]([NH:1][C:2]1[C:3]([CH3:9])=[N:4][N:5]([CH3:8])[C:6]=1[CH3:7])(=[O:19])[CH3:18]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 1616031,3,5-trimethyl-1H-pyrazol-4-amine

Product 1

HCID 22335537N-(1,3,5-trimethylpyrazol-4-yl)acetamideYield 72%

Procedure

Under anhydrous conditions, a mixture of 4-amino-1,3,5-trimethyl-1H-pyrazole (10 g, 80 mmol) and triethylamine (16.7 mL, 120 mmol) was treated dropwise with acetyl chloride (6.3 mL, 88 mmol). The reaction mixture was stirred at ambient temperature for 72 hours. The triethylamine hydrochloride was removed by vacuum filtration. The filtrate was concentrated in vacuo and the residue triturated with Et2O to give 9.6 g of title compound as a tan solid (72% yield, m.p. 118-119° C.).

Workup

  1. customThe triethylamine hydrochloride was removed by vacuum filtration
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue triturated with Et2O

Sources & evidence

ORD record
ord-3a6fe5ad730a49dc90a56e129b726971
Source dataset
uspto-grants-2004_02
Patent number
US06686476B2

Reaction notes

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