Br[C:2]([F:19])([F:18])[S:3]([C:6]1[N:10]=[CH:9][N:8]([C:11](=[O:17])[N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[N:7]=1)(=[O:5])=[O:4].[CH2:20]([S:22]SCC)[CH3:21].P([O-])([O-])(O)=O.[Na+].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>CN(C)C=O.O>[CH2:13]([N:12]([CH2:15][CH3:16])[C:11]([N:8]1[CH:9]=[N:10][C:6]([S:3]([C:2]([F:19])([F:18])[S:22][CH2:20][CH3:21])(=[O:5])=[O:4])=[N:7]1)=[O:17])[CH3:14]
To a stirred solution of 10 g (0.028 mol) 3-(bromodifluoromethylsulfonyl)-1-(N,N-diethylcarbamoyl)-1,2,4-triazole (as prepared in Example 1) and 6.81 ml (0.055 mol) diethyl disulfide in a mixture of 30 ml N,N-dimethylformamide and 20 ml water at 0° C. was added 5.9 g (0.042 mol) sodium hydrogen phosphate and 7.23 g (0.042 mol) sodium dithionite. After 2 h, the reaction mixture was diluted with 100 ml water and extracted with ethyl acetate (3×100 ml). The combined resulting organic layers were washed with saturated sodium chloride solution, dried over MgSO4 and evaporated. Preparative LC purification of the residue with 40% ethyl acetate-hexane gave 5.45 g (57% yield) of the desired 1-(N,N-diethylcarbamoyl)-3-[difluoro(ethylthio)methylsulfonyl]-1,2,4-triazole as a colorless oil having n D 25 = 1.5063 .
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