Potassium Carbonate → 2-n-Butyl-4-chloro-1-(4-bromobenzyl)-5-formylimidazole

HRID 1033604Notes

Reaction equation

HRID 1033604 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>C1(C)C=CC=CC=1.O>[CH2:1]([C:5]1[N:6]([CH2:18][C:17]2[CH:20]=[CH:21][C:14]([Br:13])=[CH:15][CH:16]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 685274-Bromobenzyl bromideHCID 178418251HCID 178418251, compound

Product 1

HCID 99505572-n-Butyl-4-chloro-1-(4-bromobenzyl)-5-formylimidazoleYield 89.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2-n-butyl-4-chloro-1H-imidazole-5-carboxaldehyde (0.6 m=111.9 g), p-bromobenzylbromide (0.6 m=153.02 g), anhydrous potassium carbonate (0.75 m=103.5 g), and dry N,N-dimethylacetamide (900 mL) was stirred at room temperature for 4 hours. The mixture was diluted with 1.2L of toluene and 1.8L of water. After mixing for half an hour, the layers were separated. The organic layer was washed two more times with 900 mL portions of water, then dried over magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated. The residual oil was pumped overnight to a weight of 191.71 g (89.9% yield).

Workup

  1. additionAfter mixing for half an hour
  2. customthe layers were separated
  3. washThe organic layer was washed two more times with 900 mL portions of water
  4. dry with materialdried over magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. concentrationthe filtrate was concentrated
  7. waitThe residual oil was pumped overnight to a weight of 191.71 g (89.9% yield)

Sources & evidence

ORD record
ord-51713b70e8fc4b618607bb248fba299c
Source dataset
uspto-grants-1994_05
Patent number
US05310928

Reaction notes

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