Reaction #3763

Reaction equation

isobutyryl chloride

p-iodoaniline

pyridine

water

Isobutyryl chloride

→

N-(4-iodophenyl)isobutyramide

Yield 97.4%

Solvents

acetonitrile

Conditions

Workup

1. 1
   FiltrationPrecipitated crystalline solids were collected by filtration

Procedure

To a dispersion of p-iodoaniline (219.0 g, 1 mol) in acetonitrile(1000 ml) was added pyridine (81.0 ml, 1 mol). Isobutyryl chloride (100.5 ml, 1 mol) was added dropwise to the mixture over 1 hour in an ice bath. The mixture was further stirred for one hour following the addition of isobutyryl chloride and to the mixture was added water (3000 ml). Precipitated crystalline solids were collected by filtration to give N-(4-iodophenyl)isobutyramide (281.7 g, Yield: 97%).

Source