1-(1H-Imidazol-1-yl)ethanone → HCID 19742900, compound

HRID 2254896Notes

Reaction equation

HRID 2254896 reaction equation
[C:1]([N:4]1[CH:8]=[CH:7]N=C1)(=[O:3])[CH3:2].N[C:10]1[CH:15]=[C:14](CC)[N:13]=[C:12]([CH2:18][CH3:19])[CH:11]=1>C1(C)C=CC=CC=1>[C:1]([NH:4][C:8]1[CH:7]=[C:14]([CH2:15][CH3:10])[N:13]=[C:12]([CH2:18][CH3:19])[CH:11]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 11789375HCID 11789375, compound

Product 1

HCID 19742900HCID 19742900, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-acetylimidazole (0.61 g) was added to a solution of 4-amino-2,6-diethylpyridine (0.61 g) in toluene (10 ml) and the mixture was heated at reflux for 16 hours. The mixture was cooled to ambient temperature and solvent was removed by evaporation. The residue was purified by flash chromatography eluting with ethyl acetate to give 4-(N-acetylamino)-2,6-diethylpyridine (B) (0.66 g) as a solid, m.p. 74°-78° C.; NMR (CDCl3): 1.26(t, 6H), 2.18(s, 3H), 2.74(q, 4H), 7.18(s, 2H), 7.75(broad s, 1H); mass spectrum (chemical ionisation, ammonia): 193(M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customsolvent was removed by evaporation
  4. customThe residue was purified by flash chromatography
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-225bda1f36ea4e1db161b7e03e4772c8
Source dataset
uspto-grants-1993_08
Patent number
US05236937

Reaction notes

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