Oxalyl chloride → 3-Methoxy-4-nitrobenzoyl isocyanate

HRID 508802Notes

Reaction equation

HRID 508802 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-3cb2c03939df4e6ea2fdfa3c4c31c991
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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