[CH3:1][N:2]([C:13]1[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19](O)=[O:20])=[CH:15][CH:14]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1.S(Cl)([Cl:27])=O>C(Cl)(Cl)Cl>[CH3:1][N:2]([C:13]1[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19]([Cl:27])=[O:20])=[CH:15][CH:14]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1A mixture of 2-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionic acid (3.0 g, 0.0087 mole; see Example 9), thionyl chloride (0.76 ml, 0.01 mole) and chloroform (25 ml) was heated under reflux for a period of 3 hours. The reaction mixture was cooled and the solvent and excess thionyl chloride was removed by distillation under reduced pressure to give the title compound.
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