Phosgene → 2,6-Xylyl isocyanate

HRID 345778Notes

Reaction equation

HRID 345778 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[C:10](Cl)(Cl)=[O:11]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[N:4]=[C:10]=[O:11]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 68962,6-Dimethylaniline

Product 1

HCID 987872,6-Xylyl isocyanateYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

7 g (0.05 mole) of 2,6-dimethyl aniline dissolved in 20 ml of toluene are added dropwise to a 20% solution of phosgene in toluene (1.5 equivalents) maintained at 0° in an ice bath. The mixture is then heated at reflux for 3 h. The mixture is concentrated and the residue is distilled under vacuum. B.p.=100°/13 mm Hg. Yield: 76%.

Workup

  1. temperaturemaintained at 0° in an ice bath
  2. temperatureThe mixture is then heated
  3. temperatureat reflux for 3 h
  4. concentrationThe mixture is concentrated
  5. distillationthe residue is distilled under vacuum

Sources & evidence

ORD record
ord-3e77c900ccd24313b17946e2ccd1a558
Source dataset
uspto-grants-1991_10
Patent number
US05059614

Reaction notes

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