Diphosgene → 4-Chloro-2,3-dihydro-2,2-dimethylbenzofuran-7-yl isocyanate

HRID 440654Notes

Reaction equation

HRID 440654 reaction equation
[NH2:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=2[C:5]([Cl:13])=[CH:4][CH:3]=1.Cl[C:15](OC(Cl)(Cl)Cl)=[O:16]>C1(C)C=CC=CC=1>[Cl:13][C:5]1[C:6]2[CH2:7][C:8]([CH3:11])([CH3:12])[O:9][C:10]=2[C:2]([N:1]=[C:15]=[O:16])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 224047737-Amino-4-chloro-2,3-dihydro-2,2-dimethylbenzofuran

Product 1

HCID 153462864-Chloro-2,3-dihydro-2,2-dimethylbenzofuran-7-yl isocyanateYield 99.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1.97 g (0.010 mole) of 7-amino-4-chloro-2,3-dihydro-2,2-dimethylbenzofuran in 60 mL of toluene was added slowly 1.2 mL (0.010 mole) of trichloromethyl chloroformate. This mixture was stirred at ambient temperature for one hour and then was heated at reflux for approximately 16 hours. At the conclusion of this period the solvent was evaporated from the reaction mixture under reduced pressure, leaving 2.23 g of 4-chloro-2,3-dihydro-2,2-dimethylbenzofuran-7-yl isocyanate as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately 16 hours
  3. customAt the conclusion of this period the solvent was evaporated from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-89ed21e2b5e043df8fc9252b13124aa5
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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