Dimethylformamide → 1-[5-Methyl-2-(4-pyridinyl)-1H-imidazol-4-yl]ethanone

HRID 569463Notes

Reaction equation

HRID 569463 reaction equation
[CH3:1][C:2](=[O:8])[C:3](=O)[C:4](=O)[CH3:5].[N:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[CH:11][CH:10]=1.C[N:18](C)C=O>>[CH3:5][C:4]1[NH:18][C:15]([C:12]2[CH:13]=[CH:14][N:9]=[CH:10][CH:11]=2)=[N:16][C:3]=1[C:2](=[O:8])[CH3:1]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 773174-PyridinemethanamineHCID 1367032,3,4-Pentanetrione

Product 1

HCID 133879391-[5-Methyl-2-(4-pyridinyl)-1H-imidazol-4-yl]ethanone

Conditions

Temperature
-10 °C

Procedure

A mixture of 6.5 g of 2,3,4-pentanetrione, 3-oxime and 6.0 g of 4-pyridylmethylamine in 75 ml of N,N-dimethylformamide was stirred at reflux temperature for 4 hours, then the solvent was removed in vacuo and 100 ml of acetonitrile was added to the residual oil. This mixture was boiled, then cooled at -10° C. The resulting precipitate was collected, washed with 50 ml of cold acetonitrile, air dried and then recrystallized from 150 ml of boiling acetonitrile after treatment with activated charcoal by cooling at -10° C., giving 4.0 g of the desired compound as a tan solid, mp 181°-183° C.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. customthe solvent was removed in vacuo and 100 ml of acetonitrile
  3. additionwas added to the residual oil
  4. customThe resulting precipitate was collected
  5. washwashed with 50 ml of cold acetonitrile, air
  6. customdried
  7. customrecrystallized from 150 ml of boiling acetonitrile after treatment with activated charcoal
  8. temperatureby cooling at -10° C.

Sources & evidence

ORD record
ord-f234247d74af4d31a6375ecca0383c2b
Source dataset
uspto-grants-1988_03
Patent number
US04732895

Reaction notes

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