[CH3:1][N:2]1[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1.[CH3:8][S:9]([OH:12])(=[O:11])=[O:10].[CH2:13]1[S:15][CH2:14]1>O>[CH3:8][S:9]([O-:12])(=[O:11])=[O:10].[CH3:1][N+:2]1([CH2:13][CH2:14][SH:15])[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1To precooled (ice bath) N-methylthiomorpholine* (5.00 g, 42.7 mmol) was added methanesulfonic acid (1.47 mL, 20.5 mmol) and ethylene sulfide (1.30 mL, 21.4 mmol). The mixture was heated at 65° C. for 24 h and diluted with water (25 mL). The aqueous solution was washed with diethyl ether (3×25 mL), pumped under vacuum and poured over a silica gel reverse phase column; the title compound being eluted with water. The appropriate fractions were combined and evaporated to afford the thiol as an oil (4.80 g, yield 86%); ir (film) νmax : 2550 cm-1 (w, SH); 1Hmr (DMSO d6)δ: 3.25-2.95 (6H, m, CH2N⊕), 3,32 (3H, s, CH3N⊕), 3.20-2.65 (7H, m, CH2S, SH) and 2.32 ppm (3H, s, CH3SO3).
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