Thionyl Chloride → HCID 86737970, compound

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Reaction Steps

A mixture of 1.0 g (2.1 mmole) of the crude 6-chloro-7,8-methylenedioxy-1-(p-sulfophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine trifluoroacetamide, 20 ml of thionyl chloride and 0.04 ml of dimethylformamide was heated at 80° for 2 hours. The thionyl chloride was evaporated in vacuo. The residue which is 6-chloro-7,8-methylenedioxy-1-(p-chlorosulfonylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine trifluoroacetamide was dissolved in tetrahydrofuran. The solution was added slowly to 40 ml of iced concentrated ammonium hydroxide. The mixture was stirred at room temperature for an hour, the pH was adjusted to 8 with hydrochloric acid and the product was extracted into ethyl acetate. The extracts were washed with water, dried, concentrated and applied to a column packed with 50 g of silica gel. The column was developed with a gradient of 24 to 35 percent of ethyl acetate in cyclohexane to give 0.5 g of 6-chloro-7,8-methylenedioxy-1-(p-sulfamylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine trifluoroacetamide. Field desorption mass spectroscopy showed an intense m/e at 476 which is consistent with the molecular ion. NMR and IR were consistent with the structure.

Provenance & Evidence