Dimethylformamide → 2-Chloro-5-nitrobenzamide

HRID 53669

Reaction equation

HRID 53669 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].ClCCl.C(Cl)(=O)C(Cl)=O.C[N:24](C)C=O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH2:24])=[O:5]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 172872-Chloro-5-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 2865622-Chloro-5-nitrobenzamide

Conditions

Temperature
25 °C

Procedure

A mixture of 2-chloro-5-nitrobenzoic acid (15.0 g, 74.0 mmol) and 200 mL of dichloromethane was reacted with oxalyl chloride (16.2 mL, 186.0 mmol) and a catalytic amount of dimethylformamide. The mixture was stirred at 25° C. for 3 hours. The solvent was removed in vacuo, and the residue was redissolved in 200 mL of dichloromethane. The solution was cooled to 0° C., and ammonia was bubbled through the cold solution for 5 minutes, whereupon the product precipitated to form solution. The product was collected by filtration to yield 6.8 g, mp 174°-175° C.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was redissolved in 200 mL of dichloromethane
  3. temperatureThe solution was cooled to 0° C.
  4. customammonia was bubbled through the cold solution for 5 minutes, whereupon the product
  5. customprecipitated
  6. customto form solution
  7. filtrationThe product was collected by filtration
  8. customto yield 6.8 g, mp 174°-175° C.

Sources & evidence

ORD record
ord-c5cf0b48a4a34299955db292eb81bf2e
Source dataset
uspto-grants-1997_04
Patent number
US05620997

Linked notes

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