Nitric Acid → 5-chloro-2-(4-nitrophenyl)-1H-Imidazole-4-carboxaldehyde

HRID 223513Notes

Reaction equation

HRID 223513 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:6]=1[CH:7]=[O:8].[N+:15]([O-])([OH:17])=[O:16].S(=O)(=O)(O)O>>[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[NH:5][C:6]=1[CH:7]=[O:8]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 178520008HCID 178520008, compound

Product 1

HCID 1785200115-chloro-2-(4-nitrophenyl)-1H-Imidazole-4-carboxaldehyde

Procedure

10 g of 4-chloro-5-formyl-2-phenylimidazole was added little by little to a mixture of 25 ml each of fuming nitric acid (specific gravity of 1.52) and concentrated sulfuric acid. After addition was completed, the mixture was stirred at room temperature for 1 hour, and poured into 400 ml of ice-water. Recrystallization of the resultant precipitate from 100 ml of dimethylformamide yielded 9 g of 4-chloro-5-formyl-2-(4-nitrophenyl)imidazole as slightly yellow, needle-formed crystals, m.p. of not lower than 300° C.

Workup

  1. additionAfter addition
  2. customRecrystallization of the resultant precipitate from 100 ml of dimethylformamide

Sources & evidence

ORD record
ord-a88e9fa5921b41d49b4ad0ea31c9271a
Source dataset
uspto-grants-1982_10
Patent number
US04355040

Reaction notes

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