Nitric Acid → 2-(4-Nitro-3-pentafluorosulfanylphenyl)isoindole-1,3-dione
Reaction equation
[F:1][S:2]([F:23])([F:22])([F:21])([F:20])[C:3]1[CH:4]=[C:5]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH:6]=[CH:7][CH:8]=1.[N+:24]([O-:27])([OH:26])=[O:25]>>[N+:24]([C:8]1[CH:7]=[CH:6][C:5]([N:9]2[C:10](=[O:19])[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]2=[O:18])=[CH:4][C:3]=1[S:2]([F:1])([F:20])([F:21])([F:22])[F:23])([O-:26])=[O:25].[N+:24]([C:6]1[CH:7]=[CH:8][C:3]([S:2]([F:23])([F:1])([F:20])([F:21])[F:22])=[CH:4][C:5]=1[N:9]1[C:10](=[O:19])[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]1=[O:18])([O-:27])=[O:25]Participants
Conditions
- Temperature
- 0 °C
Procedure
1 g (2.863 mmol) of 2-(3-pentafluorosulfanylphenyl)isoindole-1,3-dione 51.4 was dissolved at 0° C. in 3.29 ml of concentrated nitric acid, and the mixture was stirred at 0° C. for 2 h. Thereafter, the mixture was left to stand overnight at room temperature. The reaction solution was added to 50 g of ice-water and the mixture was stirred for 1 h; thereafter, the precipitate was filtered off with suction, washed with water, dried and purified by chromatography on silica gel with toluene as the eluent. 2-(4-Nitro-3-pentafluorosulfanylphenyl)isoindole-1,3-dione 51.5 with the melting point of 200-203° C. and 2-(2-nitro-5-pentafluorosulfanylphenyl)isoindole-1,3-dione 51.6 with the melting point of 175-177° C. were obtained in a ratio of 1:2.
Workup
- waitThereafter, the mixture was left
- waitto stand overnight at room temperature
- stirringthe mixture was stirred for 1 h
- filtrationthereafter, the precipitate was filtered off with suction
- washwashed with water
- customdried
- custompurified by chromatography on silica gel with toluene as the eluent
Sources & evidence
- ORD record
- ord-98799ba23d7749f1a6553e478cf5d348
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759366B2
Reaction notes
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