Oxalyl chloride → 2,6-Difluorobenzoyl isocyanate

HRID 1284934Notes

Reaction equation

HRID 1284934 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 isocyanateYield 76.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
110 °C

Procedure

In 150 ml of dichloroethane was suspended 13.5 g of 2,6-difluorobenzamide, and 14.0 g of oxalyl chloride was little by little added to the suspension, followed by heating under reflux at about 110° C. for 15 hours. The reaction mixture was concentrated under reduced pressure, and the resultant oily substance was distilled under reduced pressure to give 12 g of the subject compound as an oily material of boiling point of 123° C./60 mmHg.

Workup

  1. additionby little added to the suspension
  2. temperatureby heating
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. distillationthe resultant oily substance was distilled under reduced pressure

Sources & evidence

ORD record
ord-4602ade754a041dca1bf0b4fe05ce5be
Source dataset
uspto-grants-1986_01
Patent number
US04564639

Reaction notes

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