Acetic Anhydride → N-(1,3,5-trimethylpyrazol-4-yl)acetamide

HRID 1045980Notes

Reaction equation

HRID 1045980 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([NH2:8])[C:4]([CH3:9])=[N:3]1.[C:10]([O-])(=[O:12])[CH3:11].[K+].C(OC(=O)C)(=O)C>CCOC(C)=O>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([NH:8][C:10](=[O:12])[CH3:11])[C:4]([CH3:9])=[N:3]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 1616031,3,5-trimethyl-1H-pyrazol-4-amineHCID 517044Potassium Acetate

Product 1

HCID 22335537N-(1,3,5-trimethylpyrazol-4-yl)acetamideYield 104%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 1,3,5-trimethylpyrazol-4-amine (1 g, 7.99 mmol), potassium acetate (0.862 g, 8.79 mmol) and acetic anhydride (0.889 mL, 7.99 mmol) in EtOAc (25 mL) was stirred at 25° C. overnight. Silica gel was added and the mixture was concentrated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 5% MeOH in DCM. The solvent was evaporated to dryness to afford N-(1,3,5-trimethylpyrazol-4-yl)acetamide (1.390 g, 104%) as a off-white solid. Mass spectrum: MH+ 168

Workup

  1. additionSilica gel was added
  2. concentrationthe mixture was concentrated
  3. customThe crude product was purified by flash chromatography on silica gel eluting with 0 to 5% MeOH in DCM
  4. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-47843191ec224762bd42e15b0b00fa13
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

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