反应详情

Lithium aluminum hydride, 1.52 h. (0.04 mole), is weighed under nitrogen, transferred to a dry nitrogen-flushed reaction flask, and suspended in 50 ml. of absolute ether. A solution of 5.34 g. (0.04 mole) of aluminum chloride in 60 ml. of absolute ether is added dropwise. The mixture, containing a while precipitate, is stirred at room temperature while a solution of 4.87 g. (0.02 mole) of N-methyl-2-(phenylthio)benzamide in 1 1. of absolute ether is added dropwise. The mixture is stirred at reflux for about 18 hours. After cooling, hydrolysis is effected by the dropwise addition of 60 ml. of water. After decantation of the ethereal layer and washing of the gelatinous precipitate with boiling ether, the precipitate is suspended in 40 ml. of 40% aqueous sodium hydroxide and 200 ml. of water. The mixture is extracted repeatedly with ether-benzene (1:1). Evaporation of solvents under reduced pressure from the washed and dried organic extract leaves the product as the residual oil. The base is converted to the hydrogen maleate salt by treating an ethereal solution with a slight excess of maleic acid dissolved in absolute ethanol. The hydrogen maleate separates in white crystals, m.p. 121°-122.5° C. The melting point is unchanged upon further recrystallization.

1. customflushed
2. customreaction flask
3. additionThe mixture, containing a while precipitate
4. stirringThe mixture is stirred
5. temperatureat reflux for about 18 hours
6. temperatureAfter cooling
7. customhydrolysis
8. additionis effected by the dropwise addition of 60 ml
9. washAfter decantation of the ethereal layer and washing of the gelatinous precipitate with boiling ether
10. extractionThe mixture is extracted repeatedly with ether-benzene (1:1)
11. customEvaporation of solvents under reduced pressure from the
12. washwashed
13. extractiondried organic extract
14. customleaves the product as the residual oil
15. customThe melting point is unchanged upon further recrystallization