Phosgene → 3-(3-Phenylpropyl)phenyl isocyanate

HRID 1995476Notes

Reaction equation

HRID 1995476 reaction equation
[C:1](Cl)(Cl)=[O:2].[C:5]1([CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=2)[NH2:17])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1(C)C=CC=CC=1>[C:5]1([CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([N:17]=[C:1]=[O:2])[CH:18]=[CH:19][CH:20]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 4273073-(3-Phenylpropyl)aniline

Product 1

HCID 127905743-(3-Phenylpropyl)phenyl isocyanateYield 95.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

170 g of phosgene are dissolved in 200 ml of toluene at -10° C. 145 g of 3-(3-phenylpropyl)-aniline, dissolved in 300 ml of toluene, are slowly added dropwise at -10° C. The mixture is warmed slowly, phosgene is introduced at 60° C., and the mixture is brought to the boil. After 6 hours, excess phosgene is flushed out with nitrogen and the mixture is distilled. 156 g of 3-(3-phenylpropyl)-phenyl isocyanate, of boiling point 107°-110° C./0.1 mbar, are obtained.

Workup

  1. additionare slowly added dropwise at -10° C
  2. temperatureThe mixture is warmed slowly
  3. customexcess phosgene is flushed out with nitrogen
  4. distillationthe mixture is distilled

Sources & evidence

ORD record
ord-7c730ab013c842deb5426619e25213a0
Source dataset
uspto-grants-1983_09
Patent number
US04405358

Reaction notes

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