Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CN(C=O)C.[NH2:18][C:19]1[N:23]([CH2:24][CH3:25])[N:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C.O>[CH2:24]([N:23]1[C:19]([NH:18][C:2]2[C:3](=[CH:7][C:8]([S:11][CH3:12])=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:20][CH:21]=[N:22]1)[CH3:25]A mixture of 2-chloro-5-(methylthio)benzoic acid (8.8 g, 0.043 mol), DMF (100 mL), 5-amino-1-ethylpyrazole (4.8 g, 0.043 mol), K2CO3 (5.94 g, 0.043 mol) and Cu(OAc)2 (0.5 g ) was refluxed overnight. The reaction mixture was cooled to room temperature, poured into water and acidified with acetic acid to a pH of about 4-5. The mixture was extracted with CH2Cl2 and then the CH2Cl2 layer was evaporated to afford 4.5 g of N-(1-ethylpyrazol-5-yl)-5-(methylthio)anthranilic acid.
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