1-(2-oxo-2-phenylethyl)pyrrolidine-2,5-dione synthesis

13synthesis methods

Product Name:1-(2-oxo-2-phenylethyl)pyrrolidine-2,5-dione
CAS Number:24246-87-5
Molecular formula:C12H11NO3
Molecular Weight:217.22

128-08-5 Synthesis

128-08-5
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536-74-3 Synthesis

536-74-3
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1-(2-oxo-2-phenylethyl)pyrrolidine-2,5-dione

24246-87-5
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Yield: 71%

Reaction Conditions:

Stage #1:N-Bromosuccinimide;phenylacetylene with water at 80; for 1 h;
Stage #2: with 1,8-diazabicyclo[5.4.0]undec-7-ene in acetone at 20; for 2 h;Mechanism;Reagent/catalyst;Solvent;Temperature;

Steps:

Representative procedure for the synthesis of α-imino ketones from alkynes
To a stirred solution of phenylacetylene 1a (102.12 mg, 1.0 mmol) and H₂O (1.0 mL) in a vial (4.0 mL) were added N-Bromosuccinimide (356 mg, 2.0 mmol). Upon sealing by a septum cap and stirring at 80 °C for 1 h, the reaction mixture was then cooled to room temperature. Subsequently, acetone (1 mL) and DBU (3.0 mmol) were introduced into the reaction mixture, and the stirring was continued at room temperature for additional 2 h. After completion of reaction as monitored by TLC analysis, acetone was evaporated in vaccuo and crude product was poured into water and then extracted with CH₂Cl₂ (3×10 mL). The organic phase was washed with water (3×10 mL), dried over Na₂SO₄, filtered and concentrated in vaccuo.The crude product was purified by a short-pad silica gel column chromatography with petroleum ether as eluent to give compound 2a as a white solid (154.1 mg, 71% yield). Table 2, entry 1 2a Yield: 71% (154 mg); White solid. m.p. 160-151 °C. ¹H NMR (400 MHz, CDCl₃) δ 2.88 (s, 4H), 4.96 (s, 2H), 7.51 (t, 2H), 7.61 (t, 1H), 7.91 (d, 2H); ¹³C NMR (100 MHz, CDCl₃) δ 28.4, 44.7, 128.1, 128.9, 134.3, 176.7, 190.2.

References:

Wei, Ting;Zeng, Yongming;He, Wei;Geng, Lili;Hong, Liang [Chinese Chemical Letters,2019,p. 383 - 385] Location in patent:supporting information

100-42-5 Synthesis