[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:16])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:5][CH:4]=1.[SH:17][CH2:18][CH2:19]O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1.C(O)CCC.ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:10][N:11]3[CH:15]=[N:14][CH:13]=[N:12]3)[S:17][CH2:18][CH2:19][O:16]2)=[CH:5][CH:4]=1
To a slurry of 32.5 g 1-(4-methoxyphenyl)-2-(1H-1,2,4-triazole-1-yl) ethanone in 500 ml dry toluene and 250 ml 1-butanol was added 23.4 g 2-mercaptoethanol and 38.0 g p-toluenesulfonic acid. The thickened slurry was refluxed under a Dean-Stark trap for about 40 hours, until no more water collected. The solvent was evaporated leaving a solid residue which was dissolved in dichloromethane and washed twice with 10% aqueous sodium hydroxide and once with water. The organic layer was dried, filtered and evaporated to leave an oily residue which partially solidified on high vacuum pumping. The residue was triturated with hot toluene/cyclohexane, cooled and filtered to give 6.5 g of product.
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