Oxalyl chloride → 2-Chloro-6-fluorobenzoyl isocyanate

HRID 59236

Reaction equation

HRID 59236 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-4548ea085f674a4d899d467001b5b831
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

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