Cl.[NH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.[C:14](N1C=CN=C1)([N:16]1C=CN=C1)=[S:15].C(N(CC)CC)C.N>C(Cl)(Cl)Cl.O.CCCCCC.CO>[CH3:11][O:10][C:8]([C:7]1[CH:6]=[CH:5][C:4]([CH2:3][NH:2][C:14]([NH2:16])=[S:15])=[CH:13][CH:12]=1)=[O:9]
Under an argon atmosphere, to a suspension of methyl 4-aminomethylbenzoate hydrochloride (170.0 g, 0.843 mol) in chloroform (850 ml, 5.0 v/w) were successively added 1,1′-thiocarbonyldiimidazole (purity 90%, 166.0 g, 0.843 mol) and triethylamine (123 ml, 0.885 mol). After stirring at room temperature for 3 hr, 28% aqueous ammonia (570 ml, 8.43 mol) and methanol (170 ml, 1.0 v/w) were added and the mixture was stirred overnight. n-Hexane (1700 ml, 10.0 v/w) and water (850 ml, 5.0 v/w) were successively added to the reaction mixture and the mixture was stirred at room temperature for 3 hrs. The precipitated crystals were collected by filtration, washed successively with n-hexane (500 ml) and water (500 ml) and dried in vacuo to give the title compound (172.5 g, yield 91.3%) as a colorless solid.
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