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

HRID 586558Notes

Reaction equation

HRID 586558 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-bf3e794ce6ca44daa8910ea679bdc95e
Source dataset
uspto-grants-2005_08
Patent number
US06936630B2

Reaction notes

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