反应详情

温度

85 °C

A mixture of 4-acetylpyridine (25 ml, 226.0 mmol) and bis(dimethylamino)methoxymethane (44 ml, 293.8 mmol) was heated at 85° C. for 30 min followed by evaporation to dryness to recover a solid of 3-(dimethylamino)-1-(4-pyridyl)-3-propen-1-one. Its ethanolic solution (200 ml) was transferred into ethanolic 1.13 N sodium ethoxide (200 ml) containing urea (16.3 g, 271 mmol). The mixture was heated to reflux overnight, then cooled down to ice-bath temperature. The precipitate was filtered, dissolved in a minimal amount of water and the aqueous solution was washed with dichloromethane. The title compound was precipitated from the aqueous solution by neutralization with 6N hydrochloric acid and filtered. More material was obtained from the original reaction filtrate which was concentrated, diluted with a minimal amount of water and washed with dichloromethane. The aqueous solution was neutralized with 6N hydrochloric acid and the precipitate filtered. MS (m/z): 174.1 (M+H)+; C9H7N3O requir. 173.2.

1. customfollowed by evaporation to dryness
2. customto recover a solid of 3-(dimethylamino)-1-(4-pyridyl)-3-propen-1-one
3. temperatureThe mixture was heated
4. temperatureto reflux overnight
5. temperaturecooled down to ice-bath temperature
6. filtrationThe precipitate was filtered
7. dissolutiondissolved in a minimal amount of water
8. washthe aqueous solution was washed with dichloromethane
9. customThe title compound was precipitated from the aqueous solution by neutralization with 6N hydrochloric acid
10. filtrationfiltered
11. customMore material was obtained from the original reaction filtrate which
12. concentrationwas concentrated
13. additiondiluted with a minimal amount of water
14. washwashed with dichloromethane
15. filtrationthe precipitate filtered