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

HRID 2113434Notes

Reaction equation

HRID 2113434 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 purified by chromatography (SiO2, gradient CH2Cl2 to 35% (CH2Cl2/MeOH=9/1) to afford the tide compound as an oil that solidifies on standing (10.62 g, 79%). MS: m/e=319.2/321.3 [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. custompurified by chromatography (SiO2, gradient CH2Cl2 to 35% (CH2Cl2/MeOH=9/1)

Sources & evidence

ORD record
ord-649b80a7bbc349f2ad3eef10fbe69e9d
Source dataset
uspto-grants-2008_10
Patent number
US07432256B2

Reaction notes

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