1-Bromo-3-chloropropane → HCID 20143107, compound

Participants

Reaction Steps

To a stirred suspension of 60% sodium hydride (0.7 g) in anhydrous dimethylformamide (10 ml), 3,4-dihydro-2-(2,5-dimethoxyphenyl)-4-methyl-3-oxo-2H-1,4-benzothiazine (5.0 g) dissolved in anhydrous dimethylformamide (15 ml) is added under nitrogen atmosphere and ice-cooling, and the mixture is stirred for 20 minutes at room temperature. 1-Bromo-3-chloropropane (3.0 g) dissolved in dimethylformamide (5 ml) is added to a reaction mixture, and the mixture is stirred for 1.5 hours at 50° C. The mixture is poured into a mixture of ethyl acetate and water. The organic layer is washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is purified by silica gel column chromatography to give 5.4 g (86.9%) of the titled compound as an oily form.

Provenance & Evidence