Methylamine → N-Methylphthalimide
Reaction equation
[C:1]1(=O)[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][NH2:13]>O>[CH3:12][N:13]1[C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]2[C:1]1=[O:6]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 250 °C
Procedure
An addition funnel is charged with 46 parts of phthalic anhydride. After the anhydride is melted, it is added as a slow stream through an adaptor heated at 250° C containing a side arm. The adaptor is connected to a glass tube filled with glass beads. Through the side arm of the adaptor there is introduced methylamine gas. The mixture of the methylamine gas and the liquid phthalic anhydride is allowed to flow into the glass tube heated at 300° C which contains glass beads. At the bottom of the glass tube there is a receiver in the form of 100 ml flask fitted with a side arm. The methylamine gas is introduced at a rate of 1-2 parts per minute. The addition of the molten phthalic anhydride is completed in about 10-15 minutes while excess methylamine and water produced in the reaction being vented through the side arm. There is obtained a 72% yield of N-methylphthalimide as a white solid having a melting point of 129.5°-132° C. No unreacted phthalic anhydride and less than 1% by weight of bis-(N-methyl)amide of phthalic anhydride was detected in the final product based on liquid chromotography.
Workup
- additionit is added as a slow stream through an adaptor
- additioncontaining a side arm
- customThe adaptor is connected to a glass tube
- additionfilled with glass beads
- temperatureheated at 300° C which
- customfitted with a side arm
- customproduced in the reaction
Sources & evidence
- ORD record
- ord-247d95a7faec415aa5df3de41b0b22a2
- Source dataset
- uspto-grants-1977_04
- Patent number
- US04020089
Reaction notes
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