Phenol → 1H-1,4,7-Triazonine, octahydro-1-[(4-methylphenyl)sulfonyl]-
Reaktionsgleichung
[C:1]1([CH3:39])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:18][CH2:17][N:16](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:15][CH2:14][N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:12][CH2:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C1(O)C=CC=CC=1>Br.C(O)(=O)C>[C:1]1([CH3:39])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)(=[O:8])=[O:9])=[CH:5][CH:6]=1Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
1,4,7-Tris(p-toluenesulfonyl)-1,4,7-triazacyclononane (17.56 g, 29.7 mmol) and phenol (21 g, 223.0 mmol) are dissolved in 240 ml of a solution of HBr (33%) in glacial acetic acid. The solution is heated at 90° C. for 30 h. A solid appears after 3 h. After returning to ambient temperature, the mixture is filtered and the solid is washed with diethyl ether (2×80 ml). The hydrobromide salt is dissolved in a 1M sodium hydroxide solution until the pH is of the order of 12 units. The aqueous solution is extracted with chloroform (8×50 ml). The combined organic phases are dried over Na2SO4 and the solvent is evaporated under vacuum. Finally, a white solid is obtained (7.36 g, yield 88%).
Aufarbeitung
- customAfter returning to ambient temperature
- filtrationthe mixture is filtered
- washthe solid is washed with diethyl ether (2×80 ml)
- dissolutionThe hydrobromide salt is dissolved in a 1M sodium hydroxide solution until the pH
- extractionThe aqueous solution is extracted with chloroform (8×50 ml)
- dry with materialThe combined organic phases are dried over Na2SO4
- customthe solvent is evaporated under vacuum
- customFinally, a white solid is obtained (7.36 g, yield 88%)
Quellen und Nachweise
- ORD-Eintrag
- ord-2caf0f77d101431bafcd0a432140584f
- Quelldatensatz
- uspto-grants-2015_02
- Patentnummer
- US08945514B2
Notizen zur Reaktion
Wird geladen…