Ethanol → 4-Amino-2-pentafluorosulfanylbenzonitrile
Reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([S:20]([F:25])([F:24])([F:23])([F:22])[F:21])[CH:13]=1.O.[NH2:27]N.[CH2:29](O)[CH3:30]>>[NH2:3][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([S:20]([F:25])([F:21])([F:22])([F:23])[F:24])[CH:13]=1.[CH2:29]([N:3]([C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([S:20]([F:24])([F:25])([F:21])([F:22])[F:23])[CH:13]=1)[C:4](=[O:11])[C:5]1[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:2]([NH2:27])=[O:1])[CH3:30]Participants
Procedure
610 mg (1.63 mmol) of 4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-pentafluorosulfanylbenzonitrile 51.8 were dissolved in 30 ml of ethanol and admixed with 100 mg (1.956 mmol) of hydrazine hydrate (100%). The mixture was stirred at room temperature overnight. Thereafter, the mixture was concentrated under reduced pressure and the residue was purified by chromatography (preparative HPLC; Purospher STAR RP-18e (10 μm); eluent: acetonitrile/water (0.5% trifluoroacetic acid) 5/95→95/5 [45 min.]). 4-Amino-2-pentafluorosulfanylbenzonitrile 51.9 (1H NMR: 7.65, s, 1H, 7.2, s, 1H, 6.8, m, 3H) and N-(4-cyano-3-pentafluorosulfanylphenyl)phthalamide ethyl ester 51.10 (1H NMR: 11.3, s, 1H, 8.6, s, 1H, 8.2, d, 1H, 8.1, d, 1H, 7.95, d, 1H, 7.75, m, 1H, 7.7, m, 2H, 4.2, q, 2H, 1.15, t, 3H) were obtained.
Workup
- concentrationThereafter, the mixture was concentrated under reduced pressure
- customthe residue was purified by chromatography (preparative HPLC; Purospher STAR RP-18e (10 μm); eluent: acetonitrile/water (0.5% trifluoroacetic acid) 5/95→95/5 [45 min.])
Sources & evidence
- ORD record
- ord-49bc70cd503c40c08babdecd02e63311
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759366B2
Reaction notes
Loading…