Reaktionsgleichung
C(Cl)(=O)C(Cl)=O.CS(C)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][OH:26])=[CH:21][CH:20]=1.CCN(CC)CC>C(Cl)Cl>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][CH:20]=1Komponenten
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a solution of oxalyl chloride (0.9 ml, 10.32 mmol) in CH2Cl2 (15 ml) at −78° C. was added a solution of DMSO (1.5 ml, 21.11 mmol) in CH2Cl2 (10 ml) and the mixture allowed to stir for 20 min. at −78° C., after which [4-(Pyridin-2-ylaminomethyl)-phenyl]-methanol (1.1 g, 5.13 mmol) in CH2Cl2 (10 ml) was added dropwise. Stirring was continued for 2 hours and then Et3N (2.9 ml, 21.30 mmol) was added dropwise. The cooling bath was removed, stirring was continued for 3 h, and the mixture was diluted with 300 mL ethyl acetate, washed with sat. NaHCO3, brine and dried over Na2SO4. Evaporation of the solvent and purification of the residue by flash chromatography on silica gel, using 30% ethyl acetate in CH2Cl2, gave the title compound (335 mg, 31%) as a pure white solid.
Aufarbeitung
- stirringStirring
- waitwas continued for 2 hours
- customThe cooling bath was removed
- stirringstirring
- waitwas continued for 3 h
- additionthe mixture was diluted with 300 mL ethyl acetate
- washwashed with sat. NaHCO3, brine
- dry with materialdried over Na2SO4
- customEvaporation of the solvent and purification of the residue by flash chromatography on silica gel
Quellen und Nachweise
- ORD-Eintrag
- ord-f466dc70f6664a43a2e59685051e375f
- Quelldatensatz
- uspto-grants-2006_08
- Patentnummer
- US07084155B2
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