Réaction #3790

Équation de réaction

2-chloro-5-nitrobenzoic acid

oxalyl chloride

dimethylformamide

→

2-chloro-5-nitro benzamide

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autrethe solvent was removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue was redissolved in 200 mL of fresh dichloromethane
3. 3
   Autreammonia was bubbled into the solution for 5 minutes, whereupon the product
4. 4
   Autreprecipitated from solution
5. 5
   FiltrationThe product was collected by filtration

Mode opératoire

A mixture of 2-chloro-5-nitrobenzoic acid (15.0 g, 74.0 mmol) in 200 mL of dichloromethane was reacted at 24° C. with oxalyl chloride (16.2 mL, 186.0 mmol) and a catalytic amount of dimethylformamide. After 3 hours, the solvent was removed in vacuo, and the residue was redissolved in 200 mL of fresh dichloromethane. The solution was cooled to 0° C., and ammonia was bubbled into the solution for 5 minutes, whereupon the product precipitated from solution. The product was collected by filtration to yield 6.8 g of 2-chloro-5-nitro benzamide, mp 174°-175° C.;

Source