[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[C:11]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:12]=2[S:13][C:14]=1[C:15]([NH2:17])=[O:16].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C=O)C.C(OCC)(=O)C>[CH3:23][O:22][C:20]1[CH:19]=[CH:18][C:12]2[S:13][C:14]([C:15]([NH2:17])=[O:16])=[C:10]([S:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:11]=2[CH:21]=1Benzylmercaptan (134 μL, 1.14 mmol) is added to a suspension of 3-chloro-5-methoxybenzo[b]thiophene-2-carboxamide (250 mg, 1.03 mmol) in 2 mL of DMF. Diazabicycloundecene (DBU) (170 μL, 1.14 mmol) is added and the mixture is warmed to 50° C. After 1 hour, the reaction mixture is allowed to cool and then is diluted with ethyl acetate and washed with 1N NaOH, 1N HCl, water, and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate: hexane gives 5-methoxy-3-[(phenylmethyl)thio]benzo[b]thiophene-2-carboxamide in 63% yield; mp=151°-153° C.
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