Toluene → 2,4,6-Trimethoxyphenyl isocyanate

HRID 1198044Notes

Reaction equation

HRID 1198044 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[CH3:12][O:13][C:14]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[C:15]=1[NH2:16]>>[CH3:24][O:23][C:17]1[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=[C:14]([O:13][CH3:12])[C:15]=1[N:16]=[C:1]=[O:2]

Participants

4

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 842712,4,6-Trimethoxyaniline

Product 1

HCID 100818122,4,6-Trimethoxyphenyl isocyanate

Procedure

To a heated solution (70° C.) of phosgene in toluene (12.5% solution, 230 ML, 2.5 eq), 2,4,6-trimethoxyaniline (25.0 g, 0.113 mol) was added portionwise. The reaction mixture was heated to reflux for 4 hours and then stirred at room temperature for 16 hours. The reaction mixture then concentrated in vacuo. The residue was rinsed two times with ether and concentrated in vacuo. Ether was again added to the residue and cooled in an ice bath for 2 hours. The solid was filtered, rinsed with ether, and oven-dried to yield the desired product.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture then concentrated in vacuo
  4. washThe residue was rinsed two times with ether
  5. concentrationconcentrated in vacuo
  6. additionEther was again added to the residue
  7. temperaturecooled in an ice bath for 2 hours
  8. filtrationThe solid was filtered
  9. washrinsed with ether
  10. customoven-dried

Sources & evidence

ORD record
ord-6afa455981c24d40916782b62e6e1e3a
Source dataset
uspto-grants-1994_01
Patent number
US05278326

Reaction notes

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