5-bromo-2-(4-methyl-1H-imidazol-1-yl)benzonitrile → HCID 67548883, compound

HRID 1786179Notes

Reaction equation

HRID 1786179 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[C:14]([CH2:5][N:10]([CH3:14])[CH3:11])=[C:13]([CH3:15])[N:12]=[CH:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

3

Reactant 1

HCID 669615175-bromo-2-(4-methyl-1H-imidazol-1-yl)benzonitrile

Product 1

HCID 67548883HCID 67548883, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-2-(4-methyl-imidazol-1-yl)-benzonitrile (11.0 g, 42.0 mmol) and N,N-dimethylmethyleneiminium chloride (5.0 g, 53.4 mmol) in DMF (75 mL) was stirred at 90° C. for 16 h. The solvent was evaporated and the oily residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The organic phase was dried over sodium sulfate, concentrated and chromatographed (SiO2, dichloromethane:methanol=1000:0 to 965:35) to afford the title compound as an oil that solidifies on standing (10.62 g, 79%). MS: m/e=321.3/319.2 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. customthe oily residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customchromatographed (SiO2, dichloromethane:methanol=1000:0 to 965:35)

Sources & evidence

ORD record
ord-aa0ad0d8c8554b1ea3911e7b64043a1e
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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