Hydroxylamine → N'-hydroxy-4-(morpholin-4-yl)-3-(trifluoromethyl)benzene-1-carboximidamide
Reaktionsgleichung
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[C:15]([F:18])([F:17])[F:16])[CH2:3][CH2:2]1.[NH2:19][OH:20]>C(O)C>[OH:20][N:19]=[C:11]([NH2:12])[C:10]1[CH:13]=[CH:14][C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[C:8]([C:15]([F:18])([F:17])[F:16])[CH:9]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
To a solution of 4-morpholino-3-(trifluoromethyl)benzonitrile (17.3 g, 67.3 mmol) in ethanol (400 mL) was added a 50% aqueous solution of hydroxylamine (4.9 mL, 74.1 mmol) dropwise. The mixture was heated at about 65° C. for 24 hours. The mixture was cooled to ambient temperature and the solid was removed by filtration. The fitrate was partitioned between ethyl acetate (1.8 L) and water (1.5 L). The organic layer was washed with water (1.0 L) and brine (1.0 L) and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo to give N′-hydroxy-4-morpholino-3-(trifluoromethyl)benzimidamide (18.6 g, 91%) as a mixture of syn/anti isomers. LCMS (Table 1, Method b) Rt=1.85 min, m/z 290.15 (M+H)+; 1H NMR (DMSO-d6, 400 MHz) 9.75 (s, 1H), 8.09-8.16 (m, 1H), 7.89-7.96 (m, 1H), 7.52-7.58 (m, 1H), 3.66-3.72 (m, 4H), 2.83-2.93 (m, 4H).
Aufarbeitung
- temperatureThe mixture was cooled to ambient temperature
- customthe solid was removed by filtration
- customThe fitrate was partitioned between ethyl acetate (1.8 L) and water (1.5 L)
- washThe organic layer was washed with water (1.0 L) and brine (1.0 L)
- dry with materialdried over anhydrous magnesium sulphate
- customThe solvent was removed in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-d4c73fc42cc44e96b6a50d60d0ff061f
- Quelldatensatz
- uspto-grants-2010_11
- Patentnummer
- US07834039B2
Notizen zur Reaktion
Wird geladen…