反应 #1576

反应方程式

propargylamine

5'-amino-4'-chloro-2'-fluoroacetanilide

triethylamine

phenylchloroformate

→

title product

1-(5-Acetamido-2-chloro-4-fluorophenyl)-3-(2-propynyl)urea

溶剂

tetrahydrofuran

water

ethyl acetate

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   温度while maintaining the reaction mixture temperature at 25°-30° C
2. 2
   workup.ADDITIONAfter the addition
3. 3
   洗涤The organic mixture is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine
4. 4
   干燥dried over anhydrous magnesium sulfate
5. 5
   浓缩concentrated in vacuo
6. 6
   其他to obtain a tan solid
7. 7
   温度refluxed for 1 hour
8. 8
   过滤The aqueous mixture is filtered
9. 9
   其他to obtain a solid which
10. 10
    洗涤is washed sequentially with water, 0.5N hydrochloric acid and water
11. 11
    其他dried overnight

实验过程

A solution of 5'-amino-4'-chloro-2'-fluoroacetanilide (11.25 g, 55.6 mmol), and triethylamine (7.70 mL, 55.6 mmol) in tetrahydrofuran is added dropwise to a stirred solution of phenylchloroformate (8.70 mL, 69.4 mmol) in tetrahydrofuran while maintaining the reaction mixture temperature at 25°-30° C. After the addition is complete, the reaction mixture is stirred at room temperature for 75 minutes, and poured into ethyl acetate. The organic mixture is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a tan solid. A solution of the solid in tetrahydrofuran is treated with propargylamine (9.52 mL, 139 mmol), refluxed for 1 hour, and poured into water. The aqueous mixture is filtered to obtain a solid which is washed sequentially with water, 0.5N hydrochloric acid and water, and dried overnight to give the title product as a beige solid.

来源