[CH3:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]2[CH:10]([C:11]([OH:13])=O)[S:9][CH2:8][C:7](=[O:14])[C:6]=2[CH:15]=1.C(Cl)(=O)C(Cl)=O.[CH2:23]([O:25][P:26]([NH2:31])([O:28][CH2:29][CH3:30])=[O:27])[CH3:24].[H-].[Na+]>C1COCC1.CN(C=O)C.O>[CH2:23]([O:25][P:26]([NH:31][C:11]([CH:10]1[C:5]2[CH:4]=[C:3]([CH3:16])[C:2]([CH3:1])=[CH:15][C:6]=2[C:7](=[O:14])[CH2:8][S:9]1)=[O:13])([O:28][CH2:29][CH3:30])=[O:27])[CH3:24]To a solution of 6,7-dimethyl-3,4-dihydro-1H-2-benzothiopyran-4-one-1-carboxylic acid (0.945 g) in THF (10 ml) were added oxalyl chloride (0.609 g) and DMF (2 drops), and the mixture was stirred at room temperature for 1 hour. On the other hand, a mixture of diethoxyphosphorylamine (4.9 g), sodium hydride in oil (60%, 0.32 g) and THF (30 ml) was stirred with ice-cooling for 30 minutes and, then, the above solution was added. The mixture was stirred with ice-cooling for 30 minutes, poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and the solvent was distilled off to give N-diethoxyphosphoryl-6,7-dimethyl-3,4-dihydro-1H-2-benzothiopyran-4-one-1-carboxamide (0.29 g, 19%). Recrystallization from ethyl acetate gave colorless prisms melting at 192°-1931/2° C.
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