反応 #80703

反応方程式

propargylamine

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

triethylamine

phenylchloroformate

→

title product

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

溶媒

tetrahydrofuran

water

ethyl acetate

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

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

実験手順

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 strred 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 rection 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.

出典