Ammonia → HCID 59226972, Verbindung
Reaktionsgleichung
[NH3:1].[C:2]([C:4]1[CH:35]=[CH:34][C:7]([C:8]([NH:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14]([C:18]([F:30])([C:26]([F:29])([F:28])[F:27])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])=[CH:13][C:12]=2[CH2:31][O:32][CH3:33])=[O:9])=[CH:6][C:5]=1F)#[N:3]>CS(C)=O>[NH2:1][C:5]1[CH:6]=[C:7]([CH:34]=[CH:35][C:4]=1[C:2]#[N:3])[C:8]([NH:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([C:18]([F:30])([C:26]([F:29])([F:28])[F:27])[C:19]([F:24])([F:25])[C:20]([F:23])([F:22])[F:21])=[CH:13][C:12]=1[CH2:31][O:32][CH3:33])=[O:9]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
Ammonia gas was added for 30 minutes to a solution of 4-cyano-3-fluoro-N-[2-methoxymethyl-6-methyl-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethyl-propyl)-phenyl]-benzamide (0.981 g, 1.90 mmol) (Example I1) in dimethylsulfoxide (20 ml). The reaction mixture was heated to 100° C. for 16 hours. The reaction mixture was allowed to cool to ambient temperature and more ammonia gas was added. The reaction mixture was heated to 100° C. for a further 16 hours. The reaction mixture was allowed to cool to ambient temperature and then partitioned between water and ethyl acetate. The aqueous phase was extracted 3 times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1) to give 3-amino-4-cyano-N-[2-methoxymethyl-6-methyl-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethyl-propyl)-phenyl]-benzamide (640 mg, 66% yield). 1H-NMR (400 MHz, CDCl3): 8.77 (s, 1H), 7.51 (m, 2H), 7.37 (m, 2H), 7.18 (d, 1H), 4.63 (s, 2H), 4.49 (s, 2H), 3.37 (s, 3H), 2.36 (s, 3H) ppm.