[CH3:1][O:2][CH2:3][C:4]([NH:6][CH2:7][C:8]1[S:9][CH:10]=[CH:11][N:12]=1)=O.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][O:2][CH2:3][C:4]1[N:12]2[C:8]([S:9][CH:10]=[CH:11]2)=[CH:7][N:6]=1To 570 mg (3.1 mmol) of the above-obtained 2-(methoxyacetylamino)methylthiazole was added 5 ml of phosphorus oxychloride. The mixture was refluxed for 4 hours, cooled to room temperature, and concentrated to dryness under reduced pressure. To the residue were added 2 ml of water and 5 ml of methylene chloride to obtain a solution, to which was added 2 g of potassium carbonate little by little. The mixture was stirred for 5 minutes. The organic layer was separated, and the aqueous layer was extracted two times with methylene chloride. The combined organic layers were dried over anhydrous potassium carbonate, concentrated under reduced pressure, and purified by flash column chromatography using silica gel, eluting with ethyl acetate. A fraction containing the desired compound was concentrated to dryness. The residue was further purified by column chromatography using Sephadex LH 20, eluting with a 1:1 mixture of chloroform and methanol to give 110 mg (yield 21%) of the title compound.
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