Acetyl chloride → 1-Acetyl-4-phenylimidazole

HRID 2231253Notes

Reaction equation

HRID 2231253 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:14](Cl)(=[O:16])[CH3:15]>O1CCCC1>[C:14]([N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[CH:9]1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 178418822HCID 178418822, compound

Product 1

HCID 108214021-Acetyl-4-phenylimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-phenylimidazole in 40 ml of tetrahydrofuran was added portionwise 1.66 g of 50% sodium hydride. After stirring for 20 minutes, 2.46 ml of acetyl chloride was added over 10 minutes and the reaction mixture allowed to stir overnight at room temperature. The reaction was filtered and the filtrate concentrated to give 4 g of crude product which was purified by chromatographing on 150 g of silica gel using 5% methanol in chloroform as eluent, 2.88 g.

Workup

  1. stirringto stir overnight at room temperature
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-912abe7593c647b99ca32f4469d7bc09
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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