Reaction #55948

Reaction equation

triethylamine

formanilide

→

formanilide

aniline

Yield 84.1%

Solvents

pyridine

Conditions

Workup

1. 1
   Otherover the course of a 180 minute residence period
2. 2
   Otheris formed

Procedure

The 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.

Source