Hydrochloric Acid → 2-(2-Nitrobenzyl)-imidazole

HRID 1462169Notes

Reaction equation

HRID 1462169 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12](=[NH:16])OCC)([O-:4])=[O:3].CO[CH:19](OC)[CH2:20][NH2:21].Cl.[OH-].[Na+]>C(O)C>[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]1[NH:16][CH:19]=[CH:20][N:21]=1)([O-:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 13344902Ethyl 2-(2-nitrophenyl)acetimidate hydrochloride

Product 1

HCID 112064782-(2-Nitrobenzyl)-imidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (2,200 ml) and 5,156 g (8.81 moles) of ethyl 2-(2-nitrophenyl)acetimidate hydrochloride were charged into a 22 liter flask. The suspension was stirred under nitrogen at room temperature and 1022.9 g (9.73 moles) of aminoacetaldehyde dimethylacetal were added all at once. The mixture was stirred for 1 hour and 1,693 ml of 12N hydrochloric acid were added all at once to cause a gentle exotherm (to 40°). Heat was then applied and the temperature was maintained at 70°-80° for 30 minutes. The solution was cooled to 20° (ice-water bath) and diluted with 2,700 ml fo 10N sodium hydroxide solution to precipitate the product. The suspension was stirred at 10° for 1 hour under nitrogen atmosphere, the solid collected by filtration and washed with 3×2,000 ml of water to give 2-(2-nitrobenzyl)-imidazole, m.p. 155°-7°.

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. customa gentle exotherm (to 40°)
  3. temperatureHeat
  4. temperaturethe temperature was maintained at 70°-80° for 30 minutes
  5. additiondiluted with 2,700 ml
  6. customto precipitate the product
  7. stirringThe suspension was stirred at 10° for 1 hour under nitrogen atmosphere
  8. filtrationthe solid collected by filtration
  9. washwashed with 3×2,000 ml of water

Sources & evidence

ORD record
ord-2cdfc0526e704e7aafd983014815d125
Source dataset
uspto-grants-1984_07
Patent number
US04459232

Reaction notes

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