Phosgene → 1-Chloro-4-(isocyanatomethyl)benzene

HRID 488389Notes

Reaction equation

HRID 488389 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[C:10](Cl)(Cl)=[O:11]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:7]=[C:10]=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 660364-Chlorobenzylamine

Product 1

HCID 33723791-Chloro-4-(isocyanatomethyl)benzeneYield 119.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-chlorobenzylamine (0.50 g, 3.5 mmol) in toluene (15 mL) was added phosgene (7.3 mL, 14 mmol, 1.93 M solution in toluene). The resulting mixture was stirred at ambient temperature for 15 minutes, then heated to reflux. After 2 hours at reflux, the mixture was cooled to ambient temperature and concentrated in vacuo to afford 0.70 g (100% yield) of 4-chlorobenzylisocyanate, a compound of formula (Y), as a yellow liquid; NMR (CDCl3) 7.4-7.2 (m, 4), 4.4 (m, 2) ppm.

Workup

  1. temperatureheated to reflux
  2. temperatureAfter 2 hours at reflux
  3. temperaturethe mixture was cooled to ambient temperature
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a90914252204f7c9998471555854130
Source dataset
uspto-grants-2005_12
Patent number
US06972290B2

Reaction notes

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