Methane → Methyl 3-isocyanatophenylacetate
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.C.[O:14]=[C:15](Cl)OC(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[N:1]([C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1)=[C:15]=[O:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
Methyl 3-isocyanatophenylacetate is prepared as follows: at a temperature in the vicinity of -20° C. and under argon, 8.25 g of methyl 3-aminophenylacetate in solution in 100 cm3 of toluene are added to a suspension of 1 g of charcoal and 6 cm3 of diphosgene in 70 cm3 of toluene. The reaction mixture is stirred and maintained at -20° C. for 15 minutes, then, after returning to a temperature in the vicinity of 20° C., heated under reflux for 2 hours and 30 minutes. The mixture is then degassed by bubbling through argon for 30 minutes, filtered on Celite, rinsed with 50 cm3 of dichloromethane and concentrated under reduced pressure at a temperature in the vicinity of 50° C. 9.30 g of methyl 3-isocyanatophenylacetate are thus obtained in the form of a yellow liquid stored under argon and used as it is in subsequent syntheses.
Workup
- customMethyl 3-isocyanatophenylacetate is prepared
- customafter returning to a temperature in the vicinity of 20° C.
- temperatureheated
- temperatureunder reflux for 2 hours and 30 minutes
- customThe mixture is then degassed
- customby bubbling through argon for 30 minutes
- filtrationfiltered on Celite
- washrinsed with 50 cm3 of dichloromethane
- concentrationconcentrated under reduced pressure at a temperature in the vicinity of 50° C
Sources & evidence
- ORD record
- ord-ec61fc5678df46afb8b2dbbfeaf9ab9f
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05610144
Reaction notes
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