Nitric Acid → HCID 21269263, compound
Reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].[Cl:5][C:6]1[C:15]2[O:14][CH2:13][CH2:12][CH:11]([N:16]3[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:18]=[CH:17]3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.[N+:25]([O-])([OH:27])=[O:26]>>[N+:1]([O-:4])([OH:3])=[O:2].[Cl:5][C:6]1[C:15]2[O:14][CH2:13][CH2:12][CH:11]([N:16]3[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:18]=[CH:17]3)[C:10]=2[CH:9]=[C:8]([N+:25]([O-:27])=[O:26])[CH:7]=1Participants
Procedure
A solution of 31 parts of methyl 1-(8-chloro-2,3-dihydro-4H-1-benzopyran-4-yl)-1H-imidazole-5-carboxylate mononitrate in 260 parts of a nitric acid solution 60% was stirred for 45 minutes at room temperature (exothermic reaction). The reaction mixture was poured into crushed ice and the whole was made alkaline. The product was extracted with trichloromethane. The undissolved product was filtered off (the trichloromethane layer was set aside) and dried, yielding a first fraction of 7 parts (20.0%) of methyl 1-(8-chloro-2,3-dihydro-6-nitro-4H-1-benzopyran-4-yl)-1H-imidazole-5-carboxylate mononitrate. The trichloromethane layer, which was set aside (see above), was washed with water, dried, filtered and evaporated. The residue was converted into the nitric acid salt. The product was filtered off and dried, yielding a second fraction of 21 parts (60.2%) of methyl 1-(8-chloro-2,3-dihydro-6-nitro-4H-1-benzopyran-4-yl)-1H-imidazole-5-carboxylate mononitrate.
Workup
- custom(exothermic reaction)
- additionThe reaction mixture was poured
- custominto crushed ice
- extractionThe product was extracted with trichloromethane
- filtrationThe undissolved product was filtered off (the trichloromethane layer
- customdried
Sources & evidence
- ORD record
- ord-49a2673143614942b19375a0f5231003
- Source dataset
- uspto-grants-1989_03
- Patent number
- US04813998
Reaction notes
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