Oxalyl chloride → 2,6-Difluorobenzoyl isocyanate

HRID 26536

Reaction equation

HRID 26536 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].[F:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:9]=1[C:10]([NH2:12])=[O:11]>ClCCCl>[F:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:9]=1[C:10]([N:12]=[C:2]=[O:3])=[O:11]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 874392,6-Difluorobenzamide

Product 1

HCID 27333692,6-Difluorobenzoyl isocyanate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Oxalyl chloride (5.5 g) was added slowly to a suspension of 2,6-difluorobenzamide (6.0 g) in 1,2-dichloroethane maintained at a temperature within the range -10° to -5° C. When the addition was complete the mixture was allowed to warm to the ambient temperature, and then gradually heated to the reflux temperature and maintained thereat for a period of 16 hours. The solvent was then removed by evaporation under reduced pressure and the residual oil purified by distillation to yield 2,6-difluorobenzoyl isocyanate, b.p. 60°-61°/0.7 mm.

Workup

  1. temperaturemaintained at a temperature within the range -10° to -5° C
  2. additionWhen the addition
  3. temperaturegradually heated to the reflux temperature
  4. temperaturemaintained
  5. customThe solvent was then removed by evaporation under reduced pressure
  6. distillationthe residual oil purified by distillation

Sources & evidence

ORD record
ord-f779bab063b2461595cd6647fbefa252
Source dataset
uspto-grants-1979_04
Patent number
US04150158

Linked notes

Loading…