Benzyl Bromide → 1-benzyl-4-chloro-2-(4-nitrophenyl)-1H-imidazole-5-carbaldehyde

HRID 896944Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[NH:5][C:6]=1[CH:7]=[O:8].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:18]([N:5]1[C:6]([CH:7]=[O:8])=[C:2]([Cl:1])[N:3]=[C:4]1[C:9]1[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 4-chloro-5-formyl-2-(4-nitrophenyl)imidazole (19.7 g, 78.3 mmol), benzyl bromide (14.5 g, 85.0 mmole) and potassium carbonate (11.7 g, 85.0 mmole) in DMF (150 ml) was heated to 110° C. for 1.5 hours. The mixture was evaporated and residue was poured into cold water and was allowed to stay overnight in the refrigerator. The tarry residue was pulverized and filtered. Yield of crude title compound: 33.4 g. The product was recrystallized from ethanol (96%, 350 ml). Yield: 14.0 g. NMR confirmed the structure of the title compound, Compound 7.

Workup

customThe mixture was evaporated
additionresidue was poured into cold water
filtrationfiltered
customThe product was recrystallized from ethanol (96%, 350 ml)

Sources & evidence

ORD record: ord-4e509de8fae94207a9b304feac1d98b2
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921525B2

Reaction notes

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