反应 #543589

反应方程式

H2O

pyridine

Diethanolamine

4-methoxybenzenesulfonyl chloride

→

sulfonamide

收率 83.0%

N,N-Bis-(2-hydroxy-ethyl)-4-methoxy-benzenesulfonamide

收率 83.0%

溶剂

CH2Cl2

CH2Cl2

反应条件

后处理

1. 1
   萃取extracted with EtOAc
2. 2
   洗涤The organic layers were washed with 1M HCl and brine
3. 3
   干燥dried (MgSO4)
4. 4
   过滤filtered
5. 5
   浓缩the filtrate was concentrated
6. 6
   其他to give an oil which
7. 7
   其他was purified by column chromatography (95/5 CH2Cl2/MeOH)

实验过程

Diethanolamine (8.40 g, 80 mmol, 1.50 equiv) was dissolved in CH2Cl2 (30 mL) and pyridine (5.1 mL, 63.6 mmol, 1.2 equiv). A solution of 4-methoxybenzenesulfonyl chloride (10.9 g, 53 mmol, 1.0 equiv) n CH2Cl2 (30 mL) was added quickly and the resulting mixture was stirred at rt overnight, then poured into H2O and extracted with EtOAc. The organic layers were washed with 1M HCl and brine, dried (MgSO4), filtered, and the filtrate was concentrated to give an oil which was purified by column chromatography (95/5 CH2Cl2/MeOH) to give 12 g (83%) of the sulfonamide as an oil which crystallized on standing: 1H NMR (500 MHz) 7.75 (d, J=8.8, 2H, HAr); 6.99 (d, J=8.8, 2H, HAr); 3.87 (a, 3H, H3CO); 3.86 (t, J=4.9, 4 H, H2C(1′); 3.42 (br s, 2H, OH); 3.26 (t, J=4.9, 4H, H2C(2′)). 13C NMR (100 MHz) 163.05; 129.85; 129.37; 114.37; 62.25; 55.61; 52.90.

来源