Dimethylformamide → Benzoyl chloride, 3-nitro-

HRID 1487110Notes

Reaction equation

HRID 1487110 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].C(Cl)(=O)C([Cl:16])=O.CN(C=O)C>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([Cl:16])=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 84973-Nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 8495Benzoyl chloride, 3-nitro-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-nitrobenzoic acid (6.5 g, 38.9 mmol) in DCM (50 ml) was added oxalyl chloride (5 ml, 58.1 mmol) and DMF (0.5 ml, 6.46 mmol), respectively. The resulting mixture was stirred at room temperature until a clear solution was formed. The solvent was removed under vacuum. 3-Nitrobenzoyl chloride thus obtained was dissolved in DCM (50 ml), Et3N (10.13 ml, 72.7 mmol) and thiomorpholine (5 g, 48.5 mmol) were added at 0° C. Reaction mixture was gradually allowed to reach to room temperature and stirred for 2 hrs. The reaction mixture was concentrated under vacuum and cold water was added to the residue, the solid obtained was filtered and dried under vacuum to give the product (9.2 gm).

Workup

  1. customwas formed
  2. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-955f78183373473ea4b15f301315dbee
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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