Phosgene → 3-(3-Phenylpropyl)phenyl isocyanate

HRID 1903653

Reaction equation

HRID 1903653 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=2)[NH2:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](Cl)(Cl)=[O:18]>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([N:13]=[C:17]=[O:18])[CH:14]=[CH:15][CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 4273073-(3-Phenylpropyl)aniline

Product 1

HCID 127905743-(3-Phenylpropyl)phenyl isocyanateYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 3-(3-phenylpropyl)aniline (11.6 g) in 100 ml of toluene was dropwise added a solution of phosgene (20 g) in 100 ml of toluene at 10°-20° C. The resultant mixture was gradually heated and, after refluxed for 30 minutes, allowed to cool to room temperature. The solvent was removed under reduced pressure, and the residue was distilled under reduced pressure to give 11.6 g of 3-(3-phenylpropyl)phenyl isocyanate (yield, 89%). B.P. 121°-125° C./0.2 mmHg.

Workup

  1. temperatureafter refluxed for 30 minutes
  2. customThe solvent was removed under reduced pressure
  3. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-2b1085577a094030a811874d9fb02bcd
Source dataset
uspto-grants-1984_03
Patent number
US04437880

Linked notes

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