Ethanol → HCID 24899056, compound

Participants

Reaction Conditions

Reaction Steps

5-(4-Pyridin-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-7-ylmethylene)-thiazolidine -2,4-dione [compound of Example 3] (0.54 g, 1.5 mmol) was taken in 1,2-dimethoxyethane (45 mL) and heated to dissolve. The reaction mixture was then cooled to −5 to 0° C. and to this solution kept under nitrogen, were added pieces of aluminum foil (10×10×0.02 mm, 0.306 g, 11.3 mmol) which had been freshly dipped for 10 seconds sequentially in each of diethyl ether, ethanol, 2% aqueous mercuric chloride solution, ethanol and again diethyl ether. To the reaction mixture, water was added (0.45 mL), and stirred for 3.5 hours at −5 to 0° C. under N2 atmosphere. To this solution, celite (2.4 g) was added, stirred at room temperature for 5 min, filtered through a celite bed and washed with DMF (3×60 mL). The filtrate was concentrated to give crude material (0.820 g) which was purified by silica chromatography using 1% CH2Cl2 in MeOH, to give 5-(4-pyridin-2-yl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepin-7-yl-methyl)-thiazolidine-2,4-dione.

Provenance & Evidence