Sulfolane → HCID 13013927, compound

Participants

Reaction Steps

Suspend 3.035 gm. (10 mmole) of methyl 11-chlorodibenzo[b,f][1,4]thiazepin-3-carboxylate in 30 ml. of solfolane (tetrahydrothiophene 1,1-dioxide) and add 766 mg. (20 mmole) of sodium borohydride in small portions with stirring. Stir at room temperature for 3 hours, add a further 190 mg. (5 mmole) of sodium borohydride and continue stirring for 1 hour. Pour the reaction mixture into 100 ml. of ice-water. Extract with three 50 ml. portions of dry ether. Wash the ether extract twice with 50 ml. portions of saturated aqueous sodium chloride, dry over magnesium sulfate and evaporate to a residue. Chromatograph the residue over 100 gm. of silica gel eluting with 1:9 ethyl acetate in toluene. Recrystallize the recovered product from acetonitrile to obtain the title product. (m.p. 149°-150° C.).

Provenance & Evidence