C(N(CC)CC)C.[CH:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9]>S([O-])([O-])(=O)=O.[Cu+2].[Cu]I.[Cu](Cl)Cl.N1C=CC=CC=1>[CH:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1The procedure of Example I is repeated except that 12.65 g (125 mmoles) of triethylamine is substituted for the pyridine and a mixture of 4.12 g (25 mmoles) of anhydrous copper(II) sulfate and 0.55 g (2.8 mmoles) of anhydrous copper(I) iodide is substituted for the copper(II) chloride. A strong exotherm and a rapid pressure drop of about 1125 psi over the course of a 180 minute residence period is observed. GLC and ALC analyses indicate that 12.56 g (103.7 mmoles) formanilide is formed. Based on aniline as the limiting reagent, a selectivity of 49.3 mole % formanilide at 84.1% aniline conversion is obtained.
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