Potassium Carbonate → 4-Bromo-1-(4-cyanobenzyl)-2-methylimidazole-5-carboxaldehyde

HRID 277773Notes

Reaction equation

HRID 277773 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1)#[N:2].[Br:11][C:12]1[N:13]=[C:14]([CH3:19])[NH:15][C:16]=1[CH:17]=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.O>[Br:11][C:12]1[N:13]=[C:14]([CH3:19])[N:15]([CH2:7][C:6]2[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[C:16]=1[CH:17]=[O:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 178432447HCID 178432447, compound

Product 1

HCID 226259164-Bromo-1-(4-cyanobenzyl)-2-methylimidazole-5-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
-10 °C

Procedure

4-Cyanobenzylbromide (1.05 g, 5.39 mmol) was added to a solution of 4-bromo-2-methylimidazole-5-carboxaldehyde (1.02 g, 5.39 mmol) (Step A) in dimethylacetamide (15 mL). The solution was cooled to −10° C. and powdered potassium carbonate (0.745 g, 5.39 mmol) added. The reaction was stirred at −10° C. for 2 h, and a further 4 h at 20° C. The reaction was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, saturated brine, and dried over magnesium sulfate. Solvent evaporation yielded a white solid.

Workup

  1. customa further 4 h
  2. customat 20° C
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water, saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customSolvent evaporation
  7. customyielded a white solid

Sources & evidence

ORD record
ord-e3877268707c4c369cad73993c39a7b7
Source dataset
uspto-grants-2002_03
Patent number
US06358956B1

Reaction notes

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