Phosgene → 4-Isocyanato-1,2-dimethoxybenzene

HRID 1154553Notes

Reaction equation

HRID 1154553 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[NH2:10]>C1C=CC=CC=1>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([N:10]=[C:1]=[O:2])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

4

Reactant 2

HCID 6371Phosgene2×HCID 227703,4-Dimethoxyaniline

Product 1

HCID 35178104-Isocyanato-1,2-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Phosgene (4 eq) is bubbled at a moderate rate into a 3-neck flask containing a solution of 3,4-dimethoxyaniline (1 eq.), in benzene (2 liters). The flask is cooled in an ice bath for 15 minutes and then the solution is refluxed for 13/4 hours while excess phosgene is added. The reaction mixture is then refluxed overnight and the solvent removed under vacuum. Acetone is added and the solvent is again removed under vacuum leaving a dark brown oily residue which is distilled at 132°-134° C./0.6 mm. Yield: 22.5 g.

Workup

  1. temperatureThe flask is cooled in an ice bath for 15 minutes
  2. additionis added
  3. temperatureThe reaction mixture is then refluxed overnight
  4. customthe solvent removed under vacuum
  5. additionAcetone is added
  6. customthe solvent is again removed under vacuum
  7. customleaving a dark brown oily residue which
  8. distillationis distilled at 132°-134° C./0.6 mm

Sources & evidence

ORD record
ord-6b3d2d54badf42c39c2db9106e9572b3
Source dataset
uspto-grants-1984_12
Patent number
US04490374

Reaction notes

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