Ethanolamine → HCID 86717869, compound

Participants

Reaction Steps

3-Fluoro-4-methylbenzaldehyde (1.0 g, 6.49 mmol) and 30 mL anhydrous dichloromethane were added into a 100 mL three-necked flask and dissolved with stirring Anhydrous calcium chloride (6.0 g) and ethanolamine (1.7 g) were added, and the reaction lasted for 3-4 days at room temperature. The solid was filtered off, and the filtrate was concentrated under reduced pressure to obtain a light yellow solid residue. The residue was dissolved by adding 50 mL anhydrous ethanol. Then, 1-p-toluenesulfonyl-1-(3,5-dimethoxyphenyl) methyl isonitrile 2.6 g (8 mmol) and anhydrous THF (40 mL), tert-butylamine (2.4 mL) were added in succession, and the reaction lasted at 25-35° C. for 40 hours with stirring. The mixture was concentrated under reduced pressure, and the residue was washed by addition of 40 mL ethyl acetate, filtered and dried by suction to give a pale yellow solid, which was further purified by silica gel column chromatography (ethyl acetate:methanol=25:1) to afford the desired compound, as a white solid. Melting point: 202˜204° C.

Provenance & Evidence