S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[Cl:12][CH:13]([C:20]([O:22][CH3:23])=[O:21])[CH2:14][S:15][CH2:16][C:17]([NH2:19])=O.Cl>N1C=CC=CC=1>[Cl:12][CH:13]([C:20]([O:22][CH3:23])=[O:21])[CH2:14][S:15][CH2:16][C:17]#[N:19]Tosyl chloride (18.82 g) was added in portions to a stirred solution of 5-chloro-5-methoxycarbonyl-3-thiapentanamide (19 g), in dry pyridine (95 ml). Heat was evolved during the addition. The mixture was stirred for 4 hours, stood overnight, and poured into 4M hydrochloric acid (400 ml) and extracted with dichloromethane. The combined extracts were washed with 4M hydrochloric acid (×3) and saturated brine, dried (magnesium sulphate) and evaporated to obtain the title compound as a dark red oil (14.2 g) 1H n.m.r. δ (CDCl3) 3.28 (2H,d, J=7Hz, CH2CH), 3.45 (2H, s, CH2CN), 3.83 (3H,s,CO2Me), 4.54 (1H,t, J=7Hz, CH2CH).
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