Diphosgene → 2-Chloro-4-fluoro-5-isocyanatobenzaldehyde (O-methyl)oxime

HRID 566599Notes

Reaction equation

HRID 566599 reaction equation
[O:1]=[C:2](Cl)OC(Cl)(Cl)Cl.[CH3:9][O:10][N:11]=[CH:12][C:13]1[CH:18]=[C:17]([NH2:19])[C:16]([F:20])=[CH:15][C:14]=1[Cl:21]>C1(C)C=CC=CC=1>[CH3:9][O:10][N:11]=[CH:12][C:13]1[CH:18]=[C:17]([N:19]=[C:2]=[O:1])[C:16]([F:20])=[CH:15][C:14]=1[Cl:21]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 541229625-amino-2-chloro-4-fluorobenzaldehyde (O-methyl)oxime

Product 1

HCID 542049932-Chloro-4-fluoro-5-isocyanatobenzaldehyde (O-methyl)oxime

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

411.3 g of diphosgene (2.08 mol) were added dropwise to a solution of 383 g (1.89 mol) of 5-amino-2-chloro-4-fluorobenzaldehyde (O-methyl)oxime in 2 l of toluene. The temperature was then slowly raised to 110° C. in the course of approximately 6 hours so that the evolution of gas proceeded in a controlled manner. The mixture was subsequently refluxed for a further 5 hours. The reaction mixture was then left to cool and finally concentrated. Yield: 432 g.

Workup

  1. temperatureThe mixture was subsequently refluxed for a further 5 hours
  2. waitThe reaction mixture was then left
  3. temperatureto cool
  4. concentrationfinally concentrated

Sources & evidence

ORD record
ord-f934ea9d64f84ec2b287d6243b4afd8c
Source dataset
uspto-grants-2001_01
Patent number
US06175007B1

Reaction notes

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