Methylamine → 4,5,7-Trichloro-2-methyl-1H-isoindole-1,3(2H)-dione
Reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[C:4]([C:5](O)=[O:6])[C:3]=1[C:13]([OH:15])=O.[CH3:16][NH2:17]>C(O)(=O)C>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[C:4]2[C:5]([N:17]([CH3:16])[C:13](=[O:15])[C:3]=12)=[O:6]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 93 °C
Procedure
A mixture of 3,4,6-trichlorophthalic acid (25.01 g, 92.8 mmol) and glacial acetic acid (100 mL) was charged to a 250 mL 3-neck flask, equipped with a dry-ice condenser, thermometer, gas sparger and magnetic stirrer and maintained under an atmosphere of dry nitrogen. The mixture was heated and maintained at 50°-54° C. while methylamine (12 g, 0.4 mol) was introduced over a period of 1.5 hours. Following the addition of the methylamine, the reaction mixture was heated to 93° C. and maintained thereat for about 5 hours, then cooled to room temperature and filtered. The filter cake was washed with cold water and vacuum dried (0.2 mmHg) for 24 hours to yield 15.97 g of 3,4,6-trichloro-N-methylphthalimide as a white powder (m.p. 166°-167.5° C.).
Workup
- additionwas charged to a 250 mL 3-neck flask
- customequipped with a dry-ice condenser
- temperaturethermometer, gas sparger and magnetic stirrer and maintained under an atmosphere of dry nitrogen
- temperatureThe mixture was heated
- additionwas introduced over a period of 1.5 hours
- temperaturemaintained
- temperaturecooled to room temperature
- filtrationfiltered
- washThe filter cake was washed with cold water and vacuum
- customdried (0.2 mmHg) for 24 hours
Sources & evidence
- ORD record
- ord-62707de47bc44503b70b7680776b97d4
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05596104
Reaction notes
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