Phosgene → HCID 12861465, compound

HRID 461535Notes

Reaction equation

HRID 461535 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 1 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-67621b1dc4bb40fa94a9d5e6cd99ac45
Source dataset
uspto-grants-1977_12
Patent number
US04063025

Reaction notes

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