1-(1H-Imidazol-1-yl)ethanone → HCID 12832897, compound

HRID 2286130Notes

Reaction equation

HRID 2286130 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([Cl:13])=[CH:11][NH:10][CH:9]=1.[C:14](N1C=CN=C1)(=[O:16])[CH3:15]>CCOCC>[C:14]([N:10]1[CH:11]=[C:12]([Cl:13])[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:9]1)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 13341359HCID 13341359, compound

Product 1

HCID 12832897HCID 12832897, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The mixture of 4.35 g of 3-(2-chlorophenyl)-4-chloropyrol and 5.3 g of N-acetylimidazole was heated for 4 hours at 100° to 110° C. After cooling, the reaction mixture was dissolved in 200 ml of ether and the resulting ether solution was washed with successive, diluted hydrochloric acid and water. The ether solution was dried with anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residual crude product was purified by silicagel chromatography using mixed solvent of n-hexane and benzene (1:1) to obtain 2.5 g of the desired product (colorless crystal, m.p. 82°-84° C.).

Workup

  1. temperaturewas heated for 4 hours at 100° to 110° C
  2. temperatureAfter cooling
  3. washthe resulting ether solution was washed with successive, diluted hydrochloric acid and water
  4. dry with materialThe ether solution was dried with anhydrous sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe residual crude product was purified by silicagel chromatography
  7. additionusing mixed solvent of n-hexane and benzene (1:1)

Sources & evidence

ORD record
ord-df79f336a48a4693979524715b235386
Source dataset
uspto-grants-1982_04
Patent number
US04326881

Reaction notes

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