[NH2:1][C:2]1[C:3]([Cl:19])=[CH:4][C:5]([Cl:18])=[C:6]([N:8]2[C:12](=[O:13])[N:11]([CH:14]([F:16])[F:15])[C:10]([CH3:17])=[N:9]2)[CH:7]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].O.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:19][C:3]1[CH:4]=[C:5]([Cl:18])[C:6]([N:8]2[C:12](=[O:13])[N:11]([CH:14]([F:15])[F:16])[C:10]([CH3:17])=[N:9]2)=[CH:7][C:2]=1[NH:1][S:21]([CH3:20])(=[O:23])=[O:22]
The solid 1-(5-amino-2,4-dichlorophenyl)-4,5-dihydro-4-difluoromethyl-3-methyl-1,2,4-triazol-5(1H)-one (1.0 equiv.) and 1.2 equiv of methanesulfonyl chloride was suspended in 20 equivalent of water and the reaction mixture chilled to 10 C. Vigorous stirring was commenced and 0.05 equiv of tetrabutylammonium bromide in 0.05 equiv of toluene was added. Using a pH meter, the pH of the suspension was brought to 7.8 by adding adequate quantity of 1 molar sodium carbonate aqueous solution and dynamically maintained for 1 hour. The suspension was much reduced but not eliminated. Concentrated hydrochloric acid was added slowly to bring the pH of the reaction to 2.0 Wherein a precipitate was formed. The precipitate was collected by filtration, washed with water and dried to give the N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl] phenyl]methanesulfonamide as a white solid (0.41 equiv and 91% purity).
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