Dimethylformamide → 1-Methyl-5-phenylimidazole-2-carboxaldehyde

Reaction equation

[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][N:4]=[CH:3]1.C([Li])CCC.CN(C)[CH:20]=[O:21]>>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][N:4]=[C:3]1[CH:20]=[O:21]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 37463431-Methyl-5-phenyl-1H-imidazole

HCID 178418339Butyllithium

Product 1

HCID 224938781-Methyl-5-phenylimidazole-2-carboxaldehyde

Procedure

Using the procedure of Example 1D, 640 mg of 1-methyl-5-phenylimidazole, 1.55 ml of 2.6M n-butyllithium and 0.31 ml of dimethylformamide gave 320 mg of the desired product.

Sources & evidence

ORD record: ord-1f3c8e83675c4d4badac458933e88fa7
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04782050

Reaction notes

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