Benzaldehyde → 1-Methyl-5-nitro-2-styrylimidazole

HRID 616616Notes

Reaction equation

HRID 616616 reaction equation
CC1NC([N+]([O-])=O)=CN=1.S(OC)(OC)(=O)=O.[CH3:17][N:18]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]1[CH3:26].[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[O-]CC.[Na+]>C(O)C.C1C=CC=CC=1>[CH3:17][N:18]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]1[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 3090DimetridazoleHCID 6497Dimethyl SulfateHCID 127602-Methyl-5-nitroimidazoleHCID 2723922Sodium ethoxide

Product 1

HCID 3274861-Methyl-5-nitro-2-styrylimidazole

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

The novel compounds coming within the scope of the generic formula, supra, are readily synthesized starting with commercially available 2-methyl-5-nitroimidazole. This starting compound is allowed to react with a suitable alkylating agent, such as dimethyl sulfate, in a suitable solvent, for example benzene, to yield the compound identified as 1,2-dimethyl-5-nitroimidazole. This latter compound is in turn allowed to react with benzaldehyde in the presence of a base, for example sodium ethoxide in absolute ethanol, to yield 1-methyl-5-nitro-2-styrylimidazole.

Workup

  1. customare readily synthesized
  2. customto yield the compound

Sources & evidence

ORD record
ord-e0063f8bb45a416e9c60f9be357de68b
Source dataset
uspto-grants-1978_02
Patent number
US04075222

Reaction notes

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