Реакция #3612

Уравнение реакции

10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

2-methylphenylacetyl chloride

triethylamine

→

desired product

Выход 53.6%

N-[4(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2-methylbenzeneacetamide

Выход 53.6%

Растворители

methylene chloride

methylene chloride

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 72 hours at room temperature
3. 3
   Промывкаwashed with water, 2N citric acid, NaHCO3, and brine
4. 4
   СушкаThe reaction mixture is dried with Na2SO4
5. 5
   Фильтрацияfiltered through a pad of hydrous magnesium silicate
6. 6
   Другоеevaporated in vacuo
7. 7
   Другоеto give a solid which
8. 8
   Другоеis purified by flash chromatography
9. 9
   Другоеto give a solid which
10. 10
    Другоеis crystallized from ethyl acetate

Методика

To a stirred solution of 0.334 g of 2-methylphenylacetyl chloride 5 ml of methylene chloride is added 0.346 g of triethylamine at 0° C. After stirring for 3 minutes, 0.500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 72 hours at room temperature. The reaction mixture is diluted with 45 ml of methylene chloride and washed with water, 2N citric acid, NaHCO3, and brine. The reaction mixture is dried with Na2SO4, filtered through a pad of hydrous magnesium silicate and evaporated in vacuo to give a solid which is purified by flash chromatography using 1:1 ethyl acetate-hexane to give a solid which is crystallized from ethyl acetate to give 0.385 g of the desired product as white crystals, m.p. 198°-200° C.

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