Diphosgene → HCID 14698843, compound

HRID 1033156Notes

Reaction equation

HRID 1033156 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:13](OC(Cl)(Cl)Cl)=[O:14]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[N:4]=[C:13]=[O:14]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 1012542-Fluoro-4-nitroaniline

Product 1

HCID 14698843HCID 14698843, compoundYield 199.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 9.4 grams (0.06 mole) of 2-fluoro-4-nitroaniline in 200 mL of toluene was stirred, and 5.9 grams (0.03 mole) of trichloromethyl chloroformate was added dropwise. Upon completion of addition, the reaction mixture was warmed to reflux, where it stirred for about 18 hours. After this time the reaction mixture was cooled and concentrated under reduced pressure, yielding about 10.9 grams of 2-fluoro-4-nitrophenyl isocyanate. The reaction product was used immediately in the next step.

Workup

  1. additionUpon completion of addition
  2. temperaturethe reaction mixture was warmed
  3. temperatureto reflux
  4. temperatureAfter this time the reaction mixture was cooled
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d3564528ca1349ec87af76a47ae6d83f
Source dataset
uspto-grants-1994_05
Patent number
US05310723

Reaction notes

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