Phosgene → HCID 12861465, compound

HRID 614515Notes

Reaction equation

HRID 614515 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 100 ml. of toluene and then dry dimethylamine was passed through the solution for one hour at room temperature. The reaction mixture was concentrated under reduced pressure and the residue formed was recrystallized from a mixture of benzene and n-hexane to provide 2.58 g. of 3,5-dichloro-4-N,N-dimethylcarbamoylaminoacetophenone having a melting point of 138°-140° C.

Workup

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

Sources & evidence

ORD record
ord-0bf87f46d6cb49108b6450c92ae04f85
Source dataset
uspto-grants-1979_03
Patent number
US04145363

Reaction notes

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