反应详情

A mixture of 1.1 g (0.02 mole) of sodium methylate and 4 g (0.01 mole) of 8-chloro-6-(2-chlorophenyl)-1,2-dihydro-1-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid methyl ester in 100 ml of methanol was stirred under a drying tube for 30 min. The resulting pale yellow solution was treated with 5 ml of methyl iodide and stirred 5 hours longer at room temperature. After acidifying with acetic acid, the mixture was evaporated to dryness. The brown residue was partitioned between methylene chloride and water and the organic phase was separated, dried and evaporated to give a tan foam. Stirring the residue with 25 ml of ethanol gave a light tan solid. The solid was filtered, washed with a little ethanol and then with petroleum ether. Air drying on the funnel gave end product with mp ca. 120°. Recrystallization from ethanol gave off-white plates with mp 120°-125° (dec) which contained 1 mole of ethanol according to the analytical and spectral data. UV λ sh 212 mμ (ε=41000) max 281 (19800) ir (CHCl3) 1700 cm-1 (CO) 1720 (COOCH3) nmr (CDCl3) δ 3.60 ppm (s, 3, NCH3) 3.90 (s, 3, OCH3) 4.07 (d, 1) and 5.83 (d, 1) (AB-system, J=12 Hz, C4 --H) 7.05 (d, 1, J=2.5 Hz, C7 --H). 7.2-7.8 (m, 5, aromatic H) 8.03 (d, 1, J=8 Hz, C10 --H).

1. stirringstirred 5 hours longer at room temperature
2. customthe mixture was evaporated to dryness
3. customThe brown residue was partitioned between methylene chloride and water
4. customthe organic phase was separated
5. customdried
6. customevaporated
7. customto give a tan foam
8. customgave a light tan solid
9. filtrationThe solid was filtered
10. washwashed with a little ethanol
11. customAir drying on the funnel
12. customgave end product with mp ca. 120°
13. customRecrystallization from ethanol
14. customgave off-white plates with mp 120°-125° (dec) which