Dimethylformamide → 2-Chloro-5-nitrobenzamide

HRID 3694

Reaction equation

HRID 3694 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C(Cl)=O.C[N:21](C)C=O>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH2:21])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 172872-Chloro-5-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 2865622-Chloro-5-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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.;

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was redissolved in 200 mL of fresh dichloromethane
  3. customammonia was bubbled into the solution for 5 minutes, whereupon the product
  4. customprecipitated from solution
  5. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-2c2bf9e31bb848cdbaf04402697bce42
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Linked notes

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