Imidazole → HCID 20282802, compound

HRID 463279Notes

Reaction equation

HRID 463279 reaction equation
Br[CH2:2][C:3]([C:5]([CH3:8])([CH3:7])[CH3:6])=[O:4].[NH:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.O>CN(C)C=O>[CH3:6][C:5]([CH3:8])([CH3:7])[C:3](=[O:4])[CH2:2][C:10]1[NH:9][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 21642Bromopinacolone

Product 1

HCID 20282802HCID 20282802, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bromomethyl-t-butyl ketone (17.9 g) (ref. J. Amer. Chem. Soc , 70, 2886 (1948)) was added to a solution of imidazole (34.1 g) in 34 ml of dimethylformamide. After stirring for 1 hour, 600 ml of water was added and the aqueous mixture extracted several times with ethyl acetate. The combined extracts were dried over sodium sulfate, concentrated, and the resulting oil chromatographed on silica gel, eluting with 5% methanol in methylene chloride, to give 3,3-dimethylbutan-2-on-1-yl imidazole.

Workup

  1. extractionthe aqueous mixture extracted several times with ethyl acetate
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe resulting oil chromatographed on silica gel
  5. washeluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-62f1fcbedd6e4f06a6e5e4c8032f7b68
Source dataset
uspto-grants-1985_05
Patent number
US04518607

Reaction notes

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