Acetonitrile → 1-[5-Methyl-2-(3-methyl-4-pyridinyl)-1H-imidazol-4-yl]ethanone

HRID 569461Notes

Reaction equation

HRID 569461 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][NH2:9].[CH3:10][C:11](=O)[C:12](=O)[C:13](=[O:15])[CH3:14].C(#[N:20])C>>[CH3:10][C:11]1[NH:20][C:8]([C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[CH3:1])=[N:9][C:12]=1[C:13](=[O:15])[CH3:14]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 1367032,3,4-PentanetrioneHCID 1514375(3-Methylpyridin-4-yl)methanamine

Product 1

HCID 133879411-[5-Methyl-2-(3-methyl-4-pyridinyl)-1H-imidazol-4-yl]ethanone

Conditions

Temperature
-10 °C

Procedure

A mixture of 7.1 g of 3-methyl-4-pyridylmethylamine, 6.25 g of 2,3,4-pentanetrione, 3-oxime and 125 ml of acetonitrile was stirred at reflux temperature for 5 hours, then cooled at -10° C. The resulting precipitate was collected, washed with cold acetonitrile, dried and then recrystallized from a mixture of chloroform and hexane, giving 4.5 g of the desired compound, mp 185°-187° C.

Workup

  1. temperatureat reflux temperature for 5 hours
  2. customThe resulting precipitate was collected
  3. washwashed with cold acetonitrile
  4. customdried
  5. customrecrystallized from a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-1486c872b6b24c16a62454ad92699538
Source dataset
uspto-grants-1988_03
Patent number
US04732895

Reaction notes

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