Oxalyl chloride → Benzoyl isocyanate, 2-chloro-4-fluoro-

HRID 887895Notes

Reaction equation

HRID 887895 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(Cl)(=O)[C:13](Cl)=[O:14]>ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([N:6]=[C:13]=[O:14])=[O:5]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 5228982-Chloro-4-fluorobenzamide

Product 1

HCID 11521269Benzoyl isocyanate, 2-chloro-4-fluoro-Yield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.64 g (6 mmol) of 2-chloro-4-fluorobenzamide were dissolved in 3 ml of dichloromethane and, at 0° C. and under a nitrogen atmosphere, 0.8 ml (9.3 mmol) of oxalyl chloride was added, and the mixture was heated to reflux for 9 hours. The reaction mixture was concentrated under high vacuum and afforded 1.17 g (5.8 mmol) of the desired product, which was employed as solution in dichloromethane (1 mmol in 1.7 ml of solution) in stage b.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 9 hours
  3. concentrationThe reaction mixture was concentrated under high vacuum

Sources & evidence

ORD record
ord-a6e6fdec1ffb4fef80867eba3eabc620
Source dataset
uspto-grants-2012_08
Patent number
US08247452B2

Reaction notes

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