تفاعل #47772

معادلة التفاعل

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

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةis heated
2. 2
   درجة الحرارةat reflux for 16 hours
3. 3
   درجة الحرارةAfter an additional 3 hours refluxing
4. 4
   تركيزthe reaction mixture is concentrated
5. 5
   workup.DISSOLUTIONThe residue is dissolved in HCl (6N, 5 mL)
6. 6
   تركيزthe reaction mixture is concentrated
7. 7
   workup.STIRRINGThe mixture is stirred for 30 minutes
8. 8
   استخلاصextracted with CH2Cl2
9. 9
   أخرىdried
10. 10
    تركيزconcentrated
11. 11
    أخرىpurified by column chromatography (silica gel, eluting with 7N NH3 in methanol:dichloromethane from 2% to 4%)

الإجراء التجريبي

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.

المصدر