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

HRID 654337
Notes
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Reaction equation

HRID 654337 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 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 1.2 L of toluene and 1.8 L 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-5d8b35c8ec5e497ba1e05979e93fda44
Source dataset
uspto-grants-1992_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05130439

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes