[OH:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:9][C:4]=2[C:3]=1[CH2:18][CH2:19][CH3:20].[H-].[Na+].CN(NC(Cl)=[S:28])C.[CH3:30][N:31]([CH3:34])[CH:32]=O>C(Cl)Cl>[CH3:34][N:31]([C:32](=[S:28])[O:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:9][C:4]=2[C:3]=1[CH2:18][CH2:19][CH3:20])[CH3:30]Ethyl 7-hydroxy-4-oxo-8-n-propyl-4H-1-benzopyran-2-carboxylate (1 g) in anhydrous dimethylformamide (4 ml) is cooled to 0° and treated under nitrogen with sodium hydride (50% dispersion in mineral oil, 180 mg) with stirring for 30 minutes. Dimethylaminothiocarbamylchloride (465 mg) is added and the mixture is stirred 15 minutes at 0°, warmed to 80° and maintained as such for 18 hours. The mixture is cooled, diluted with methylene chloride (50 ml) and washed with water (3×100 ml)), dried over sodium sulfate and reduced to dryness in vacuo. The residue is recrystallized from ethyl acetate and hexane to yield the title compound.
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