[Cl:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[C:5](O)=O.[NH2:15][NH:16][C:17]([NH2:19])=[S:18].O=P(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[Cl:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:5]2[S:18][C:17]([NH:19][CH:2]3[CH2:3][CH2:4][CH2:8][CH2:9][CH2:10]3)=[N:16][N:15]=2)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1To a mixture of 3-chloro-2,6-dimethoxybenzoic acid (2.3 mmol, 500 mg), thiosemicarbazide (5b) (2.3 mmol, 399 mg) in anhydrous dioxane (10 mL) at 70° C. to 80° C., POCl3 (2.3 mmol, 215 μL) was added, and the mixture was warmed at 95° C. for 5 hours. The solvent was removed by distillation under reduced pressure to give a crude material which was basified at pH 8-7 with a saturated solution of NaHCO3. The precipitate obtained was collected by filtration, washed with water, and dried under vacuum. The solid was subjected to flash chromatography eluting with ethyl acetate/cyclohexane to give 115 mg of the title compound. Yield: 14%.
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