Diphosgene → 5-Isocyanato-1,2,3-trimethoxybenzene

HRID 2260186Notes

Reaction equation

HRID 2260186 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].Cl[C:15](OC(Cl)(Cl)Cl)=[O:16]>C1(C)C=CC=CC=1>[CH3:13][O:12][C:8]1[CH:7]=[C:5]([N:6]=[C:15]=[O:16])[CH:4]=[C:3]([O:2][CH3:1])[C:9]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 322853,4,5-Trimethoxyaniline

Product 1

HCID 5177665-Isocyanato-1,2,3-trimethoxybenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

600 ml of a solution of 18.3 g of 3,4,5-trimethoxyaniline in toluene was added to 140 ml of a solution of 48 ml of trichloromethyl chloroformate in toluene and the mixture was refluxed for 3 h. After cooling, the solvent was distilled off and the residue was distilled under reduced pressure (115° C./1 mmHg) to obtain 15.53 g of 3,4,5-trimethoxyphenyl isocyanate.

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off
  4. distillationthe residue was distilled under reduced pressure (115° C./1 mmHg)

Sources & evidence

ORD record
ord-6161ef20f24a4a089543c3d17d55890c
Source dataset
uspto-grants-1995_12
Patent number
US05476863

Reaction notes

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