Aminoacetaldehyde dimethyl acetal → 2-(3-nitrophenyl)-1H-imidazole

HRID 322064Notes

Reaction equation

HRID 322064 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7](=[NH:10])OC)([O-:3])=[O:2].CO[CH:16](OC)[CH2:17][NH2:18]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]2[NH:18][CH:17]=[CH:16][N:10]=2)[CH:11]=[CH:12][CH:13]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 122008323-nitro-benzimidic acid methyl ester

Product 1

HCID 8210012-(3-nitrophenyl)-1H-imidazoleYield 48.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of methyl 3-nitrobenzimidate (7.57 g) and aminoacetaldehyde dimethylacetal (5.57 g) in methanol (20 ml) is heated under reflux for 24 hours. The cool solution is evaporated, and the residue treated with water (9.5 ml) and conc. hydrochloric acid (21 nil). The mixture is heated (steam bath) for 15 minutes and evaporated under reduced pressure. Water (50 ml) is added to the residue and the insoluble solid filtered and washed with water. The filtrate is neutralized with potassium carbonate solution and the precipitated solid filtered and washed with water. The combined solids are charcoaled and recrystallised from ethanol to give 3.87 g of 2-(3nitrophenyl)imidazole, mp 193-194.5° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe cool solution is evaporated
  3. additionthe residue treated with water (9.5 ml) and conc. hydrochloric acid (21 nil)
  4. temperatureThe mixture is heated (steam bath) for 15 minutes
  5. customevaporated under reduced pressure
  6. additionWater (50 ml) is added to the residue
  7. filtrationthe insoluble solid filtered
  8. washwashed with water
  9. filtrationthe precipitated solid filtered
  10. washwashed with water
  11. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-c2438538b363415a82764565feb8661b
Source dataset
uspto-grants-2001_04
Patent number
US06211220B1

Reaction notes

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