Toluene → 2,4,6-Trimethoxyphenyl isocyanate
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
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
- temperature