[S:1]1[C:5]([NH2:6])=[N:4][CH:3]=[N:2]1.[OH-].[Na+].Cl[S:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1Cl)(=[O:12])=[O:11].[ClH:23]>O1CCOCC1.O>[Cl:23][C:20]1[CH:21]=[C:13]([S:10]([NH:6][C:5]2[S:1][N:2]=[CH:3][N:4]=2)(=[O:12])=[O:11])[CH:14]=[CH:15][C:16]=1[C:17]([OH:19])=[O:18]
1,2,4-Thiadiazol-5-amine (770 mg, 7.61 mmol, 1.5 eq) was dissolved in dioxane (10 ml), a solution of sodium hydroxide (550 mg, 14 mmol, 2.7 eq) in water (3 ml) was added and the reaction mixture stirred at room temperature for 10 minutes. 4-(chlorosulfonyl)-3-chlorobenzoic acid (Preparation 41, 1.3 g, 5.1 mmol, 1 eq) was added portionwise and the reaction mixture stirred at room temperature for 2 hours. The mixture was dropped into 2M HCl (10 ml) and concentrated in vacuo up to apparition of a solid. The resultant precipitate was discarded and filtrate filtered again to yield the title compound as a white solid (243.3 mg, 0.763 mmol, 15%).
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