Phenyl isocyanate → 2-Dimethylaminoethyl N-phenylcarbamate
Reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][N:11]([CH2:13][CH2:14][OH:15])[CH3:12]>>[C:1]1([NH:7][C:8](=[O:9])[O:15][CH2:14][CH2:13][N:11]([CH3:12])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
3
Procedure
With cooling, 128 g of phenyl isocyanate are added dropwise to 96 g of dimethylaminoethanol at 60°-70° C. in the course of 45 minutes. After a further 30 minutes at 65° C., low boiling constituents are removed at a pressure of 0.02 torr and a bath temperature of 90° C. The residue (218.4 g=97.6%) is a light yellow fluid and consists substantially of the above ester. Titration: 1 equivalent=208.4 g (theory 208.2). IR spectrum 3320 cm-1NH, 1720 cm-1C=O; no bands between 2000 and 2500 cm-1, i.e. isocyanate is no longer present. Small amounts of 5-10 g can be distilled in a bulb tube at 135° C./0.015 torr; larger amounts decompose on distillation.
Workup
- temperatureWith cooling
- customlow boiling constituents are removed at a pressure of 0.02 torr and a bath temperature of 90° C