Hydrochloric Acid → 2-(2-Nitrobenzyl)-imidazole
Reaction equation
C(O)C.Cl.[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15](=[NH:19])OCC)([O-:7])=[O:6].CO[CH:22](OC)[CH2:23][NH2:24].Cl>[OH-].[Na+]>[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]1[NH:19][CH:22]=[CH:23][N:24]=1)([O-:7])=[O:6]Participants
Procedure
Ethanol (2,200 ml) and5,156 g (8.81 moles) of ethyl 2-(2-nitrophenyl)acetimidate hydrochloride are charged into a 22 liter flask. The suspension is stirred under nitrogen at room temperature and 1022.9 g (9.73 moles) of aminoacetaldehyde dimethylacetal are added all at once. The mixture is stirred for 1 hour and 1,693 ml of 12N hydrochloric acid are added all at once to cause a gentle exotherm (to 40°). Heat is then applied and the temperature is maintained at 70°-80° for 30 minutes. The solution is cooled to 20° (ice-water bath) and diluted with 2,700 ml of 10N sodium hydroxide solution to precipitate the product. The suspension is 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
- stirringThe mixture is stirred for 1 hour
- customa gentle exotherm (to 40°)
- temperatureHeat
- temperaturethe temperature is maintained at 70°-80° for 30 minutes
- customto precipitate the product
- stirringThe suspension is stirred at 10° for 1 hour under nitrogen atmosphere
- filtrationthe solid collected by filtration
- washwashed with 3×2,000 ml of water
Sources & evidence
- ORD record
- ord-2fd0c2ea782b4bcaa761b7cff97eddb4
- Source dataset
- uspto-grants-1985_03
- Patent number
- US04507311
Reaction notes
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