Methyl chloroformate → N-(Methoxycarbonyl)maleimide
Reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH:3]=[CH:2]1.CN1CCOCC1.[CH3:15][O:16][C:17](Cl)=[O:18]>C(OCC)(=O)C>[CH3:15][O:16][C:17]([N:5]1[C:4](=[O:6])[CH:3]=[CH:2][C:1]1=[O:7])=[O:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Maleimide (2.00 g, 20.6 mmol) and N-methyl morpholine (2.08 g, 20.6 mmol) in ethyl acetate were cooled to 0° C. Dropwise addition of methylchloroformate (1.4 mL, 20.7 mmol) produced white precipitate. The solution was stirred for 1 hour at 0° C., after which the solids were removed by filtration. Concentration of the filtrate yielded a pink oil, which was purified by column chromatography (eluant 3:1 hexanes:ethyl acetate) to yield pale yellow crystals.
Workup
- customproduced white precipitate
- customafter which the solids were removed by filtration
- customConcentration of the filtrate yielded a pink oil, which
- customwas purified by column chromatography (eluant 3:1 hexanes:ethyl acetate)
- customto yield pale yellow crystals
Sources & evidence
- ORD record
- ord-aa17fb1a04cd404bb8559949b4d2b476
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802450B2
Reaction notes
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