反应 #617792

反应方程式

[2-amino-1-(3-methoxy-phenyl)-ethylsulfanyl]-acetic acid methyl ester

methyl 2-bromo-2-(3-methoxyphenyl)acetate

2-aminoethanethiol

potassium carbonate

→

2-(3-methoxyphenyl)thiomorpholin-3-one

收率 83.0%

溶剂

H2O

ethanol

反应条件

后处理

1. 1
   其他to give a light yellow suspension
2. 2
   温度The mixture was further heated
3. 3
   温度at reflux for an additional 4.5 h
4. 4
   其他Reaction mixture
5. 5
   萃取extracted with EtOAc (3×300 mL)
6. 6
   洗涤The combined organic layers were washed with brine
7. 7
   干燥dried over MgSO4
8. 8
   浓缩concentrated in vacuo
9. 9
   其他The resulting pale yellow solid was triturated with cold ether
10. 10
    其他dried under vacuum

实验过程

In a 500 mL round-bottomed flask, methyl 2-bromo-2-(3-methoxyphenyl)acetate (5.2 g, 20.1 mmol), 2-aminoethanethiol (1.55 g, 20.1 mmol) and potassium carbonate (5.55 g, 40.1 mmol) were combined with ethanol (150 ml) to give a light yellow suspension. The resultant mixture was stirred at 85° C. (bath temp.) for 2.5 h. No starting material remained. The intermediate, [2-amino-1-(3-methoxy-phenyl)-ethylsulfanyl]-acetic acid methyl ester, was the major product with 25% of the cyclized product. The mixture was further heated at reflux for an additional 4.5 h. Complete by LCMS. Reaction mixture was allowed to cool to room temperature and sit overnight. The reaction mixture was poured into 500 mL H2O and extracted with EtOAc (3×300 mL). The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting pale yellow solid was triturated with cold ether and dried under vacuum to afford 2-(3-methoxyphenyl)thiomorpholin-3-one (3.7 g, 83%) as a yellow solid. (M+H)+=224 m/e. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.88 (td, J=5.81, 2.78 Hz, 2H) 3.67 (td, J=5.81, 3.54 Hz, 2H) 3.82 (s, 3H) 4.63 (s, 1H) 6.42 (br. s., 1H) 6.85 (ddd, J=8.34, 2.53, 0.76 Hz, 1H) 7.00 (t, J=2.15 Hz, 1H) 7.01-7.05 (m, 1H) 7.29 (t, J=7.93, 1H).

来源