Hydrochloric Acid → 2,6-Difluorobenzoyl isocyanate

HRID 638350Notes

Reaction equation

HRID 638350 reaction equation
[F: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].Cl>C(Cl)Cl>[F: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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 874392,6-Difluorobenzamide

Product 1

HCID 27333692,6-Difluorobenzoyl isocyanate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

36.1 g (0.23 mol) of 2,6-difluorobenzamide are suspended in 360 ml of methylene chloride, and 53.7 g (0.42 mol) of oxalyl chloride are then added dropwise in the course of 20 minutes. After the release of hydrochloric acid has finished, the mixture is well stirred overnight under reflux. The solvent is subsequently distilled off, and the residue is distilled through a 10 cm Vigreux column at about 80° C./0.3 mm; yield 37.4 g (89%) of a slightly yellow liquid.

Workup

  1. temperatureunder reflux
  2. distillationThe solvent is subsequently distilled off
  3. distillationthe residue is distilled through a 10 cm Vigreux column at about 80° C./0.3 mm

Sources & evidence

ORD record
ord-e1ed4e202d0f452ea05ae9680f8896e7
Source dataset
uspto-grants-1985_12
Patent number
US04560770

Reaction notes

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