Dimethylformamide → 2-Nitrobenzoyl chloride

HRID 1024331Notes

Reaction equation

HRID 1024331 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](O)=[O:7])([O-:3])=[O:2].CN(C)C=O.C(Cl)(=O)C([Cl:21])=O>C(Cl)Cl>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([Cl:21])=[O:7])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 110872-Nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 118752-Nitrobenzoyl chlorideYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the suspension of 2-nitrobenzoic acid (200 g) and a catalytic amount of dimethylformamide (DMF; 5 mL) in DCM (2.5 L) was added oxalyl dichloride (304 g) dropwise at room temperature over a 30 minute interval. After the addition, the reaction was continued stirring for approximately 1 hour at room temperature and the suspension turned into a clear solution. The completion of the reaction was monitored by TLC (generally ˜1 hour). The reaction mixture was then concentrated at 35° C. to dryness to give 225 g of the crude product (13) as light yellow oil or solid (mp: 17° C., lit), which was directly used for the next step without further purification.

Workup

  1. additionAfter the addition
  2. customgenerally ˜1 hour
  3. concentrationThe reaction mixture was then concentrated at 35° C. to dryness

Sources & evidence

ORD record
ord-f3a73f6a8c9d458bbedd05f62edf52f0
Source dataset
uspto-grants-2014_05
Patent number
US08722886B1

Reaction notes

Loading…