Oxalyl chloride → 2,6-Difluorobenzoyl isocyanate

HRID 67057

Reaction equation

HRID 67057 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]>ClC(Cl)C>[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

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 874392,6-Difluorobenzamide

Product 1

HCID 27333692,6-Difluorobenzoyl isocyanate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 1.7 g. of 2,6-difluorobenzamide in 50 cc of dichloroethane was heated to 50° C. and 4.2 g. of oxalyl chloride was added dropwise with stirring and the reaction was continued for 1 hour with stirring to obtain 2,6-difluorobenzoyl isocyanate. Then, dichloroethane and excess of oxalyl chloride were distilled off under a reduced pressure. The residue was admixed with 50 cc of dioxane and a solution of 3.3 g. of 3-ethoxycarbonyl-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy) aniline in dioxane was added dropwise and the reaction was continued for 2 hours with stirring. After the reaction, the reaction mixture was poured into water and the resulting crystal was filtered and washed with water and dried to obtain 4.8 g. of the object compound having a melting point of 183°-186° C.

Workup

  1. stirringwith stirring

Sources & evidence

ORD record
ord-1e1a3187d6ab4575bb9dc5431156d266
Source dataset
uspto-grants-1982_08
Patent number
US04344951

Linked notes

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