HRID1708388

反应详情

EQUATION

反应方程式

HRID 1708388 反应方程式

AUXILIARIES

试剂、催化剂与溶剂

2

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

5-(4,5-diphenyl-1H-imidazol-2-ylthio)-pentanoic acid (3.73 g, 10.58 retool) was dissolved in 40 mL dry dimethylformamide, and treated with solid hydroxybenzotriazole hydrate (1.77 g, 13.10 retool). Then, a 20 mL dimethylformamide solution of N,N-diethylethylenediamine (2.00 mL, 14.24 mmol) was added dropwise. The mixture was cooled to 0° C., and solid dicyclohexylcarbodiimide (2.81 g, 13.62 mmol) was added in small portions over 20 minutes. The mixture was allowed to slowly warm and stirred for 48 hours, then poured into 150 mL ethyl acetate. This mixture was washed with water (3×150 mL), and the water washings were back-extracted in sequence with ethyl acetate (150 mL). The organic phases were combined, dried over anhydrous sodium sulfate, and evaporated to afford a pale yellow oil. The oil was separated by flash chromatography (1:4 methanol-methylene chloride) to afford N-[2-(diethylamino)ethyl]-5-(4,5-diphenyl-1H-imidazol-2-ylthio)-pentanamide (3.77 g, 8.37 mmol, 79%). 1 H NMR (300 MHz, CDCl3): 7.56-7.49 (4H, m); 7.33-7.17 (6H, m); 6.91 (1H, br s); 3.16 (2H, br d, J=6 Hz); 2.97 (2H, t, J=7 Hz); 2.68-2.49 (6H, m); 2.29 (2H, t, J=6 Hz); 2.00-1.57 (4H, m); 1.02 (6H, t, J=7 Hz).

WORKUP

后处理

  1. temperatureto slowly warm
  2. washThis mixture was washed with water (3×150 mL)
  3. extractionthe water washings were back-extracted in sequence with ethyl acetate (150 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customto afford a pale yellow oil
  7. customThe oil was separated by flash chromatography (1:4 methanol-methylene chloride)