2-Ethyl-6-methylaniline → 1H-Pyrrole-2,5-dione, 1-(2-ethyl-6-methylphenyl)-
Reaction equation
[C:1]([OH:8])(=O)/[CH:2]=[CH:3]\[C:4](O)=[O:5].[CH2:9]([C:11]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:12]=1[NH2:13])[CH3:10]>C(OC(C)C)(C)C>[CH2:9]([C:11]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:12]=1[N:13]1[C:4](=[O:5])[CH:3]=[CH:2][C:1]1=[O:8])[CH3:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
196 g of maleic acid arthydride were dissolved in 2.5 l of diisopropyl ether at room temperature. A solution of 270.4 g of 2-ethyl-6-methyl-aniline in 200 ml of diisopropyl ether was added dropwise at room temperature in the course of 4 hours, the resulting suspension was cooled to 15° to 20° C. and the solid was filtered off with suction and introduced into a mixture of 670 ml of acetic arthydride and 65 g of anhydrous sodium acetate. The suspension formed was heated to 100° C., while stirring, stirred at this temperature for 30 minutes, subsequently cooled to 30° C. and introduced into 1.3 l of ice-water. The precipitate was filtered off with suction, washed with ice-water and petroleum ether and dried. 321 g of N-(2-ethyl-6-methylphenyl)-maleimide (92.9% of theory) with a content of 97.8% by weight (determined by HPLC) and a melting point of 84.5° to 85° C. were obtained.
Workup
- temperaturethe resulting suspension was cooled to 15° to 20° C.
- filtrationthe solid was filtered off with suction
- additionintroduced into a mixture of 670 ml of acetic arthydride and 65 g of anhydrous sodium acetate
- customThe suspension formed
- stirringstirred at this temperature for 30 minutes
- temperaturesubsequently cooled to 30° C.
- filtrationThe precipitate was filtered off with suction
- washwashed with ice-water and petroleum ether
- customdried
Sources & evidence
- ORD record
- ord-40bdc9ff28a8496286ed19e33d390376
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05684163
Reaction notes
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