反応 #47772

反応方程式

N-(2,2-diethoxyethyl)carbodiimide

3-trifluoromethyl-benzamide

methanesulfonic acid

N-(2,2-diethoxyethyl)carbodiimide

methanesulfonic acid

→

title compound

N-[3-(1H-Imidazol-2-ylamino)-4-methyl-phenyl]-3-trifluoromethyl-benzamide

溶媒

ethanol

反応条件

後処理

1. 1
   温度is heated
2. 2
   温度at reflux for 16 hours
3. 3
   温度After an additional 3 hours refluxing
4. 4
   濃縮the reaction mixture is concentrated
5. 5
   workup.DISSOLUTIONThe residue is dissolved in HCl (6N, 5 mL)
6. 6
   濃縮the reaction mixture is concentrated
7. 7
   workup.STIRRINGThe mixture is stirred for 30 minutes
8. 8
   抽出extracted with CH2Cl2
9. 9
   その他dried
10. 10
    濃縮concentrated
11. 11
    その他purified by column chromatography (silica gel, eluting with 7N NH3 in methanol:dichloromethane from 2% to 4%)

実験手順

A mixture of N-(2,2-diethoxyethyl)carbodiimide (398 mg, 2.51 mmol), 3-amino-4-methyl-phenyl]-3-trifluoromethyl-benzamide (649 mg, 2.20 mmol), methanesulfonic acid (143 μL, 2.20 mmol) in ethanol (25 mL) is heated at reflux for 16 hours. An additional portion of N-(2,2-diethoxyethyl)carbodiimide (525 mg, 3.32 mmol) and methanesulfonic acid (143 μL, 2.20 mmol) are added. After an additional 3 hours refluxing, the reaction mixture is concentrated. The residue is dissolved in HCl (6N, 5 mL) and ethanol (5 mL). After stirring overnight, the reaction mixture is concentrated and basified with 25% NaOH solution to a pH of 14. The mixture is stirred for 30 minutes, extracted with CH2Cl2, dried, concentrated and purified by column chromatography (silica gel, eluting with 7N NH3 in methanol:dichloromethane from 2% to 4%) to give the title compound.

出典