Triethylamine → 2,2,6-Trimethyl-2,3-dihydrobenzofuran-7-yl isocyanate

HRID 1439927Notes

Reaction equation

HRID 1439927 reaction equation
[NH2:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:13].Cl[C:15](Cl)([O:17]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C>C(Cl)(Cl)(Cl)Cl>[CH3:12][C:8]1([CH3:11])[CH2:7][C:6]2[CH:5]=[CH:4][C:3]([CH3:13])=[C:2]([N:1]=[C:15]=[O:17])[C:10]=2[O:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 106073987-Amino-2,2,6-trimethyl-2,3-dihydrobenzofuran

Product 1

HCID 189850842,2,6-Trimethyl-2,3-dihydrobenzofuran-7-yl isocyanate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

A 400 mg amount of 7-amino -2,2,6-trimethyl-2,3-dihydrobenzofuran was dissolved in 10 ml of carbon tetrachloride, and 246 mg of triphosgene was added thereto. The reaction solution was heated to 80° C., and 229 mg of triethylamine was slowly added thereto with stirring. Further, the mixture was heated under reflux for 1.5 hr. The reaction mixture was filtered through Celite to remove insolubles. The solvent was removed by evaporation to provide 461 mg of the title compound.

Workup

  1. temperatureFurther, the mixture was heated
  2. temperatureunder reflux for 1.5 hr
  3. filtrationThe reaction mixture was filtered through Celite
  4. customto remove insolubles
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-22a34678f4ee403ba781ec158b3702de
Source dataset
uspto-grants-1996_03
Patent number
US05496853

Reaction notes

Loading…