4-Nitrobenzamide → 4-nitrobenzoylisocyanate

HRID 1489664Notes

Reaction equation

HRID 1489664 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].[N+:7]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([NH2:16])=[O:15])=[CH:12][CH:11]=1)([O-:9])=[O:8]>ClCCCl>[N+:7]([C:10]1[CH:11]=[CH:12][C:13]([C:14]([N:16]=[C:2]=[O:3])=[O:15])=[CH:17][CH:18]=1)([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 120914-NitrobenzamideHCID 65578Oxalyl chloride

Product 1

HCID 108994614-nitrobenzoylisocyanate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

48 ml of oxalyl chloride were added batchwise to a solution of 50 g of 4-nitrobenzamide in 1.2 l of 1,2-dichloroethane and the reaction mixture was boiled for 17 hours with reflux. For workup, the reaction mixture was concentrated and the remaining residue distilled under a high vacuum. 56 g of 4-nitrobenzoylisocyanate were obtained as colorless crystals.

Workup

  1. temperaturewith reflux
  2. concentrationFor workup, the reaction mixture was concentrated
  3. distillationthe remaining residue distilled under a high vacuum

Sources & evidence

ORD record
ord-85e312609fd44012ad4d717d617d7a68
Source dataset
uspto-grants-1997_10
Patent number
US05679699

Reaction notes

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