Реакция #447066

Уравнение реакции

acetonitrile

indomethacin

product

N-(2-Hydroxyethyl)-3-Pyridinecarboxamide

dicyclohexylcarbodiimide

dicyclohexylcarbodiimide

→

N-(2-{[1-(p-Chlorobenzoyl)- 5-methoxy-2-methyl-3-indolyl]acetoxy}ethyl)-3-pyridinecarboxamide

Выход 65.2%

Растворители

ether

Условия реакции

Обработка

1. 1
   workup.DISSOLUTIONThe first two reactants were dissolved completely
2. 2
   workup.WAITto continue for 48 hours
3. 3
   ДругоеThe precipitate (1.2 g) was removed by vacuum filtration
4. 4
   ДругоеThe solvent was removed from the filtrate under reduced pressure
5. 5
   Другоеleaving an oily residue
6. 6
   ФильтрацияIt was filtered
7. 7
   Другоеair-dried
8. 8
   Другоеrecrystallized from ethanol/ether
9. 9
   Фильтрацияfiltered
10. 10
    Промывкаwashed with ether, and air
11. 11
    Другоеdried
12. 12
    Другоеgiving a 65.2% yield

Методика

A reaction of indomethacin (1.79 g, 5.00 mmol) and the product of Example 91 (0.830 g, 5.00 mmol) was carried out, using dicyclohexylcarbodiimide (1.10 g, 5.50 mmol) as the coupling agent and acetonitrile as the solvent. The first two reactants were dissolved completely and the solution was then cooled to 0° C. The dicyclohexylcarbodiimide was added and the mixture was stirred overnight. The reaction was allowed to continue for 48 hours. The precipitate (1.2 g) was removed by vacuum filtration. The solvent was removed from the filtrate under reduced pressure leaving an oily residue. The product was solidified by stirring with anhydrous ether. It was filtered, air-dried and recrystallized from ethanol/ether. The final product was vacuum filtered, washed with ether, and air dried. The product weighed 1.65 g, giving a 65.2% yield; mp 123°-125° C.

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