Phosgene → HCID 12861465, compound

HRID 614516Notes

Reaction equation

HRID 614516 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH2:11])=[C:6]([Cl:12])[CH:5]=1)=[O:3].[C:13](Cl)(Cl)=[O:14]>C1(C)C=CC=CC=1>[C:2]([C:4]1[CH:5]=[C:6]([Cl:12])[C:7]([N:11]=[C:13]=[O:14])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 6048121-(4-Amino-3,5-dichlorophenyl)ethan-1-one

Product 1

HCID 12861465HCID 12861465, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5 g. of 4-amino-3,5-dichloroacetophenone, 5 ml. of phosgene, and 30 ml. of toluene was heated to 150° C. for 24 hours in a sealed tube. The reaction mixture was cooled and concentrated under reduced pressure to provide crude 4-acetyl-2,6-dichlorophenyl isocyanate. The crude product was dissolved in 150 ml. of toluene and then 5 ml. of aniline was added to the solution. The crystals thus formed were recovered by filtration and recrystallized from ethanol to provide 4.56 g. of 3,5-dichloro-4-phenylcarbamoylaminoacetophenone having a melting point of 239°-240° C.

Workup

  1. additionA mixture of 5 g
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c804889a125044e88ac1cce34da1ea25
Source dataset
uspto-grants-1979_03
Patent number
US04145363

Reaction notes

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