[H-].[Na+].[SH:3][C:4]1[S:5][CH:6]=[CH:7][N:8]=1.[Cl:9][C:10]1[CH:11]=[C:12]([N+:17]([O-])=O)[CH:13]=[CH:14][C:15]=1F.O>CN(C)C=O>[Cl:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][C:15]=1[S:3][C:4]1[S:5][CH:6]=[CH:7][N:8]=1)[NH2:17]To a suspension of 3.8 g sodium hydride (60% in mineral oil) in 100 ml of dimethylformamide was added slowly a solution of 10.0 g of 2-mercapto thiazole in 100 ml of dimethylformamide. After 15 min a solution of 15.0 g 3-chloro-4-fluoro nitrobenzene in 50 ml of dimethylformamide was added. After 4 hrs, the mixture was poured into water. The resulting solid was collected, washed with water, and dried in vacuum. This material was mechanically stirred at reflux in a mixture of 830 ml of methanol, 230 ml of water, 37.0 g of ammonium chloride, and 30.1 g of iron powder for 4 hrs. The boiling mixture was filtered. The solvent was removed from the filtrate and the residue was extracted with hot ethyl acetate. The ethyl acetate solution was filtered through a short silica gel column. The solvent was removed and the residue was recrystallized from ether hexane giving 17.7 g of an off white solid.: mass spectrum electrospray, m/e): M+H 243.1.
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