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

HRID 1414243Notes

Reaction equation

HRID 1414243 reaction equation
NC1N(C)N=[C:4]([C:8]2[N:9]([CH3:16])[C:10]([N+:13]([O-:15])=[O:14])=[CH:11][N:12]=2)[C:3]=1[C:17]#N.CC1NC([N+]([O-])=O)=CN=1.S(OC)(OC)(=O)=O.CN1C([N+]([O-])=O)=CN=C1C.C(=O)[C:46]1[CH:51]=[CH:50]C=[CH:48][CH:47]=1.[O-]CC.[Na+]>C(O)C.C1C=CC=CC=1>[CH3:16][N:9]1[C:10]([N+:13]([O-:15])=[O:14])=[CH:11][N:12]=[C:8]1[CH:4]=[CH:3][C:17]1[CH:50]=[CH:51][CH:46]=[CH:47][CH:48]=1

Participants

9

Reactant 6

HCID 240BenzaldehydeHCID 3090DimetridazoleHCID 6497Dimethyl SulfateHCID 127602-Methyl-5-nitroimidazole2×HCID 2723922Sodium ethoxideHCID 203681595-Amino-1-methyl-3-(1-methyl-5-nitro-2-imidazolyl)pyrazole-4-carbonitrile

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

This intermediate, the 5-amino-1-methyl-3-(1-methyl-5-nitro-2-imidazolyl)pyrazole-4-carbonitrile, is readily synthesized starting from commercially-available 2-methyl-5-nitroimidazole. The 2-methyl-5-nitroimidazole 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. customto yield the compound

Sources & evidence

ORD record
ord-00fc4f05fff94668a771e422511609b8
Source dataset
uspto-grants-1977_01
Patent number
US04001230

Reaction notes

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