Oxalyl chloride → 3-Methoxy-4-nitrobenzoyl isocyanate

HRID 59310Notes

Reaction equation

HRID 59310 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([NH2:8])=[O:7].C(Cl)(=O)[C:16](Cl)=[O:17]>C(Cl)CCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([N:8]=[C:16]=[O:17])=[O:7]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 110633383-Methoxy-4-nitrobenzamide

Product 1

HCID 900189023-Methoxy-4-nitrobenzoyl isocyanateYield 88.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-methoxy-4-nitrobenzamide (1.00 g, 5.10 mmol) in EDC (10 mL) was added oxalyl chloride (0.64 g, 6.12 mmol). The reaction mass was refluxed for 24 h. Excess of solvent was removed under vacuum to afford 1.0 g of desired product.

Workup

  1. temperatureThe reaction mass was refluxed for 24 h
  2. customExcess of solvent was removed under vacuum

Sources & evidence

ORD record
ord-79465695b451461e8748a8148dacec36
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

Loading…