[CH3:1][O:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]([CH2:9][NH:10][C:11]([NH2:13])=[S:12])=[CH:7][CH:6]=1)=[O:4].Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=O.C(=O)(O)[O-].[Na+].O>C(#N)C.CCCCCC>[N+:26]([C:23]1[CH:24]=[CH:25][C:20]([C:18]2[N:13]=[C:11]([NH:10][CH2:9][C:8]3[CH:14]=[CH:15][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=3)[S:12][CH:17]=2)=[CH:21][CH:22]=1)([O-:28])=[O:27]
To a suspension of 1-(4-methoxycarbonylbenzyl)-2-thiourea (138.0 g, 0.554 mol) obtained in Example 1(1) in acetonitrile (1380 ml, 10.0 v/w) were successively added 2-bromo-4′-nitroacetophenone (124.1 g, 0.554 mol) and sodium bicarbonate (46.9 g, 0.559 mol), and the mixture was heated under reflux for 2 hr. After cooling to room temperature, water (1380 ml, 10.0 v/w) and n-hexane (690 ml, 5.0 v/w) were successively added and the mixture was stirred for 1 hr. The precipitated crystals were collected by filtration, washed successively with water (1000 ml) and n-hexane (500 ml) and dried in vacuo to give the title compound (183.9 g, yield 89.9%) as a yellow solid.
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