Oxalyl chloride → 2-Chloro-6-fluorobenzoyl isocyanate

HRID 508726Notes

Reaction equation

HRID 508726 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([NH2:6])=[O:5].C(Cl)(=O)[C:13](Cl)=[O:14]>C(Cl)CCl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([N:6]=[C:13]=[O:14])=[O:5]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 985642-Chloro-6-fluorobenzamide

Product 1

HCID 130517312-Chloro-6-fluorobenzoyl isocyanateYield 91,106.602%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-chloro-6-fluorobenzamide (2.0 g, 0.011 mmol) in EDC (10 mL) was added oxalyl chloride (2.18 g, 0.017 mmol). The reaction mass was refluxed for 24 h. Excess of solvent was removed under vacuum to afford 2.0 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-0820864e80534bdb9430b8e948041a85
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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