반응 #4899
ord-2aa2b529cc9e41ec87acb8746e1f89c9
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반응물
시약
반응 조건
후처리
- 1온도the mixture was heated
- 2온도at reflux for 24 hr
- 3온도The reaction mixture was cooled
- 4농축The mixture was concentrated under reduced pressure
- 5여과The mixture was filtered
- 6농축the filtrate was concentrated
- 7workup.DISSOLUTIONThe residue was dissolved in 500 ml of chloroform and to this solution
- 8온도The mixture was heated
- 9온도at reflux for 48 hr
- 10온도cooled with an ice/acetone bath
- 11기타did not exceed 25° C
- 12건조finally dried over magnesium sulfate
- 13기타The solvent was evaporated under reduced pressure
- 14기타to give a black solid
- 15기타The solid was purified on a silica gel column
실험 절차
To a solution of 19.2 g (0.48 mole) of sodium hydroxide in 500 ml of water was added 60 g (0.24 mole) of 5-methoxy-2-[(1-methyl-3-pyrrolidinyl)oxy]-benzamide and the mixture was heated at reflux for 24 hr. The reaction mixture was cooled and the pH adjusted to 6.8 with concentrated hydrochloric acid. The mixture was concentrated under reduced pressure and the residue was boiled in isopropyl alcohol for 1 hour. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in 500 ml of chloroform and to this solution was added 114 g (0.96 mole) of thionyl chloride. The mixture was heated at reflux for 48 hr, then cooled with an ice/acetone bath. To the mixture was added dropwise 97 g (0.96 mole) of triethylamine at such a rate that the temperature did not exceed 25° C. The reaction solution was washeed in sequence with water, 3N hydrochloric acid solution, water, 15% aqueous sodium hydroxide and water and finally dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give a black solid. The solid was purified on a silica gel column using ethyl acetate as the eluting solvent to give on isolation 15 g (23%) of beige colored product, m.p. 98°-100° C.