1-Methylimidazole → (1-Methyl-1H-imidazol-2-yl)(phenyl)methanone

HRID 875202Notes

Reaction equation

HRID 875202 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(#N)C>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:14]

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 12325240(1-Methyl-1H-imidazol-2-yl)(phenyl)methanoneYield 92.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-methylimidazole (10.0 g, 122 mmol) in acetonitrile (120 mL) was added benzoyl chloride (14.1 mL, 122 mmol) followed by triethylamine (17.0 mL, 122 mmol), while keeping the internal temperature at 5° C. The mixture was stirred 18 h at room temperature. After filtration, the filtrate was concentrated in vacuo, diluted with ethyl acetate (200 mL) and sequentially washed with sat. aq. sodium bicarbonate (150 mL), water (100 mL) and brine (100 mL). The organic layer was dried over MgSO4 and concentrated in vacuo.to afford (1-methyl-1H-imidazol-2-yl)(phenyl)methanone [21.0 g, yield 83%; HPLC/MS: m/z=187 (M+H); log P(HCOOH)=1.38].

Workup

  1. customat 5° C
  2. filtrationAfter filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. additiondiluted with ethyl acetate (200 mL)
  5. washsequentially washed with sat. aq. sodium bicarbonate (150 mL), water (100 mL) and brine (100 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo.to

Sources & evidence

ORD record
ord-0c927385c33e4ab4a660860ae4ff4a8a
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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