Benzylmaleimide

off-white to light yellow

General Procedure: Benzylamine (17 mmol) was added dropwise into a solution of maleic anhydride (20 mmol) in AcOH (10 mL) at room temperature and the resulting suspension was stirred at reflux (overnight). Solvent was removed under reduced pressure and the residue was partitioned between CHClTo a stirred solution of furan-2, 5-dione (20.0 g, 204.0 mmol) in EtO (500.0 ml) was added dropwise phenylmethanamine (32.8 g, 306.0 mmol) in Et20 (50 ml) at 5—lO °C. The reaction mixture was stirred at room temperature for 16 h. The crystallized acid was filtered and washed with Et20, then added to a mixture of acetic anhydride (40 ml) and CH3COOK (4.0 g). The suspension was heated on a steam bath (70 °C ) for 16 h, dissolved in CH2CI2 (400ml), washed with aq.NaHCO3 (2 x 500 ml) and concentrated. The residue was purified by column chromatography (PE/EtOAc =10/1) to give the desired product as a white solid (12.6 g, yield: 33percent).1H NMR (400 MHz, CDCI3) 7.35—7.28 (m, 5H), 6.70 (s, 2H), 4.67 (s, 2H), Maleic anhydride (0.98 g, 10 mmol) dissolved in glacial acetic acid (15 ml) in, side electromagnetic stirring and slowly instillment animal pen amine (0.83 g, 6 . 67 mmol), the reaction liquid is heated to 120 °C stirring reflux 4 h. TLC detection reaction has been substantially completely, stop stirring, cooled to the room temperature, for a dilute sodium hydroxide solution prepared (8g/100 ml) diluted in and the reaction solution, ethyl acetate (30 ml × 3) extraction three times, the collection of organic phase, the organic phase dried with anhydrous sodium sulfate 12 h. Filtering, environment friendly with silica gel column chromatography, eluting agent is ethyl acetate: petroleum ether=1:10, to obtain white solid 0.41 g, yield 30.0percent.To a suspension of cis-butenedioic anhydride (1b) (49 g, 0.5 mol)in 600mL AcOH was added benzylamine (54 g, 0.5 mmol). The reactionwas then heated to reflux for 5 h. The reaction mixture wasconcentrated and the residue was dissolved in 300 mL EtOAc. TheEtOAc layerwaswashed with saturated aqueous NaHCO3 and brine.The organic layer was dried over anhydrous Na2SO4, concentratedin vacuum, purified by flash chromatography (petroleum ether:-EtOAc 8:1) to afford 1-benzyl-1H-pyrrole-2, 5-dione as a whitesolid (26.9 g, 29percent). M.p.: 58-60 °C. 1H NMR (400 MHz, CDCl3) d 4.65(s, 2H), 6.68 (s, 2H), 7.24-7.30 (m, 5H); 13C NMR (100 MHz, CDCl3)d 41.4, 127.8, 128.3, 128.7, 134.2, 136.1, 170.4; HRMS (ESI) m/z calcdfor C11H9NO2[MH] 188.0706, found 188.0709.

Molecular Weight:187.19
XLogP3:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:187.063328530
Monoisotopic Mass:187.063328530
Topological Polar Surface Area:37.4
Heavy Atom Count:14
Complexity:259
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes