S(Cl)(Cl)=O.[C:5]([OH:13])(=O)[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([CH:21]=1)[NH2:20].[OH-].[Na+]>C(N(CC)CC)C.O1CCCC1>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([CH:21]=1)[NH:20][C:5](=[O:13])[C:6]1[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=1A 100 ml. portion of thionyl chloride is added dropwise to 28.0 g. of isonicotinic acid over 30 minutes. After an additional 30 minutes the mixture becomes homogeneous. The volatiles are removed in vacuo, 250 ml. of benzene is added and then removed to leave a residue. This residue is suspended in 300 ml. of dry tetrahydrofuran and a solution of 25.0 g. of 5-chloro-2-phenoxyaniline in 63 ml. of triethylamine is added dropwise over 30 minutes and the mixture is stirred overnight. The mixture is poured into 500 ml. of 1 N-sodium hydroxide. The organic layer is separated. The basic layer is extracted with two 100 ml. portions of ether. The ether extracts and organic layer are combined, washed with 250 ml. of water and then with four 200 ml. portions of 10% hydrochloric acid. The combined acid washings are neutralized with concentrated ammonium hydroxide and extracted with three 250 ml. portions of ether. These ether extracts are dried and evaporated yielding 5'-chloro-2'-phenoxyisonicotinanilide as a brown solid.
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