Sulfolane → HCID 13013927, compound

Reaction equation

Cl[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12][C:7]=2[S:6][C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[N:3]=1.S1(=O)(=O)CCCC1.[BH4-].[Na+]>>[CH:9]1[C:8]2[CH2:2][NH:3][C:4]3[CH:20]=[CH:19][CH:18]=[CH:17][C:5]=3[S:6][C:7]=2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=1

Participants

Reactant 3

HCID 31347Sulfolane

HCID 4311764Sodium borohydride2×

HCID 13013926HCID 13013926, compound

Product 1

HCID 13013927HCID 13013927, compound

Procedure

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.).