[CH3:1][C:2]([NH:6][S:7]([CH2:10][CH2:11][CH2:12][Cl:13])(=[O:9])=[O:8])([CH3:5])[C:3]#[N:4].[Cl:14][CH:15]([S:20]Cl)[C:16](Cl)([Cl:18])[Cl:17].[OH-].[Na+].C(Cl)[Cl:25]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:25][C:15]([Cl:14])([S:20][N:6]([C:2]([C:3]#[N:4])([CH3:1])[CH3:5])[S:7]([CH2:10][CH2:11][CH2:12][Cl:13])(=[O:8])=[O:9])[CH:16]([Cl:18])[Cl:17]
To a stirred mixture of 2.25 g (0.01 mole) 2-methyl-2-(3-chloropropylsulfonamido)propionitrile (the product of Example 35) and 2.87 g (0.011 mole) tetrachloroethylsulfenyl chloride with 0.1 g benzyltriethylammonium chloride in 100 ml methylene chloride, 0.48 g [(0.012 mole) 0.96 g as a 50% weight/weight solution] sodium hydroxide dissolved in 20 ml water was added slowly. The reaction mixture was stirred for three hours. The mixture was washed three times with 100 ml water. The organic layers were dried over calcium sulfate and evaporated to give a dark brown oil which crystallized upon standing overnight. The crystals were washed with hexane to give the above-identified product, as a brown solid, melting point 68°-71° C.
Loading…
