反应详情

A stirred mixture of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (10.0 g, 31.06 mmoles) (from Preparation No. 1A), anhydrous potassium carbonate (12.84 g, 93.16 mmoles), sodium iodide (4.66 g, 31.06 mmoles) and 2-chloroethyl methyl sulfide (3.70 ml, 4.10 g, 37.26 mmoles) in 60 ml of dry DMF was refluxed for 10 hours. The solvent was evaporated under reduced pressure and the dark semi-solid was partitioned between water and methylene chloride. Sodium hydroxide solution was added to bring the pH of the aqueous layer to 14. The mixture was shaken well and the layers were separated. The aqueous layer was extracted with 3 portions of methylene chloride. The combined organic solutions were dried over MgSO4 and evaporated. The solid obtained was dissolved in 100 ml of warm acetonitrile. The solution was treated with Darco G-60, filtered, evaporated to 30 ml, and stored at -15°. The solid was filtered to give 3.56 g (32%) of the title compound as off-white crystals, mp. 118°-120°.

1. temperaturewas refluxed for 10 hours
2. customThe solvent was evaporated under reduced pressure
3. customthe dark semi-solid was partitioned between water and methylene chloride
4. additionSodium hydroxide solution was added
5. customthe layers were separated
6. extractionThe aqueous layer was extracted with 3 portions of methylene chloride
7. dry with materialThe combined organic solutions were dried over MgSO4
8. customevaporated
9. customThe solid obtained
10. filtrationfiltered
11. customevaporated to 30 ml
12. customstored at -15°
13. filtrationThe solid was filtered