反应 #594791

反应方程式

ammonium thiocyanate

4-nitrobenzoyl chloride

acetone

acetone

4-fluoro-N-methylaniline

→

1-(4-fluorophenyl)-1-methyl-3-(4-nitrobenzoyl)thiourea

反应条件

后处理

1. 1
   温度the reaction solution was heated
2. 2
   温度at reflux for 15 min
3. 3
   其他The reaction solution was removed
4. 4
   温度from heating
5. 5
   温度to maintain
6. 6
   温度reflux
7. 7
   温度heating
8. 8
   其他to give an orange oil
9. 9
   其他that separated
10. 10
    过滤The solid was collected by filtration
11. 11
    洗涤washed with water
12. 12
    其他dried

实验过程

A solution of 3.8 g (50 mmol) of ammonium thiocyanate in 100 mL of acetone was treated with a solution of 8.4 g (45 mmol) of 4-nitrobenzoyl chloride in 50 mL of acetone and the reaction solution was heated at reflux for 15 min. The reaction solution was removed from heating and 5.2 g (41 mmol) of 4-fluoro-N-methylaniline was added at such a rate as to maintain reflux, then heating was renewed for 15 min. The reaction mixture was poured onto 400 g of ice to give an orange oil that separated and solidified on standing. The solid was collected by filtration, washed with water and dried to give 1-(4-fluorophenyl)-1-methyl-3-(4-nitrobenzoyl)thiourea which was suspended in 500 mL of MeOH and treated with 2 mL (64 mmol) of hydrazine for 18 h. The byproduct 4-nitrobenzohydrazide was removed by filtration and the organic solvent was removed from the product in vacuo. The residue was dissolved in 500 mL of 8:1:1 (v/v/v) EtOAc/CHCl3/MeOH, washed thrice with 10% (w/v) aqueous HCl, then dried over a mixture of solid MgSO4 and solid Na2CO3, filtered and concentrated to give the desired compound. MS (M+H)+ 185.

来源