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

HRID 1282216Notes

Reaction equation

HRID 1282216 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-2ede8a7b860a40c9bf6022cc1df0d541
Source dataset
uspto-grants-2002_09
Patent number
US06455566B1

Reaction notes

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