2-Methyl-4-nitrophenyl isocyanate → HCID 59847714, compound
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]=[O:13]>CS(C)=O>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]([N:11]2[C:12](=[O:13])[N:11]([C:3]3[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=3[CH3:1])[C:12](=[O:13])[N:11]([C:3]3[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=3[CH3:1])[C:12]2=[O:13])=[C:2]([CH3:1])[CH:7]=1)([O-:10])=[O:9]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
To 2-methyl-4-nitrophenylisocyanate (36.0 g) in a 250 ml flask was added DMSO (50 ml) and the flask was sealed with a glass stopper which was kept in place with a plastic clip. The flask was immediately lowered into an oil bath heated to 85° C. and the dark brown reaction solution was heated for 16 h 30 min. The oil bath was removed and the reaction solution was allowed to cool to room temperature before being poured into water (800 ml), sonicated, and the precipitate was filtered off. The filter cake was added to ethanol (500 ml) and was refluxed for 4 hours, then allowed to cool to room temperature and the product was filtered off to give an off-white powder (28.1 g, 78%).
Workup
- customthe flask was sealed with a glass stopper which
- customThe flask was immediately lowered into an oil bath
- temperaturethe dark brown reaction solution was heated for 16 h 30 min
- customThe oil bath was removed
- temperatureto cool to room temperature
- additionbefore being poured into water (800 ml)
- customsonicated
- filtrationthe precipitate was filtered off
- additionThe filter cake was added to ethanol (500 ml)
- temperaturewas refluxed for 4 hours
- temperatureto cool to room temperature
- filtrationthe product was filtered off
Sources & evidence
- ORD record
- ord-e79159ad2a154178bf83be3d04ad18fa
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08951502B2
Reaction notes
Loading…