HRID372299

反应详情

EQUATION

反应方程式

HRID 372299 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

2

PROCEDURE

实验过程

Meanwhile, in a second flask, 4.6 g. of sodium are dissolved in 100 ml. of ethanol and treated at 0° C. with 34.5 g. of 2-diethylaminoethyl chloride hydrochloride. After dilution with 50 ml. of dimethylformamide and stirring for 30-40 minutes in an ice-bath, the obtained fine suspension is added dropwise at 0°-2° C. over a period of 15-20 minutes to the sodium derivative of 5-chloro-3-phenyl-isoindole-1-carboxylic acid ethyl ester prepared as in the foregoing paragraph. The mixture is subsequently stirred for 30 minutes at room temperature and then heated at 60° C. for 3 hours. After cooling, the mixture is poured into 4 liters of ice-water, 200 g. of sodium chloride are added and the separated oily product is immediately extracted with methylene chloride. The organic phase, shielded from daylight, is washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and concentrated to dryness. The resulting oil is then taken up in 200 ml. of ether, treated with 280 ml. of 0.5-N hydrochloric acid and thoroughly shaken. After cooling in an ice-bath, the crystallized hydrochloride is removed by filtration under suction, washed with water and ether and then dissolved in 700 ml. of methylene chloride. The aqueous layer is separated; the organic phase is dried over sodium sulfate, filtered and treated portionwise with 450 ml. of ether, whereby there is obtained 5-chloro-2-[2-(diethylamino)ethyl]-3-phenylisoindole-1-carboxylic acid ethyl ester hydrochloride in the form of colorless crystals having a melting point of 248°-250° C. (decomposition). Crystallization from methylene chloride/ether does not increase the melting point.

WORKUP

后处理

  1. temperatureheated at 60° C. for 3 hours
  2. temperatureAfter cooling
  3. extractionthe separated oily product is immediately extracted with methylene chloride
  4. washis washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness
  7. additionof ether, treated with 280 ml
  8. stirringof 0.5-N hydrochloric acid and thoroughly shaken
  9. temperatureAfter cooling in an ice-bath
  10. customthe crystallized hydrochloride is removed by filtration under suction
  11. washwashed with water and ether
  12. dissolutiondissolved in 700 ml
  13. customThe aqueous layer is separated
  14. dry with materialthe organic phase is dried over sodium sulfate
  15. filtrationfiltered
  16. additiontreated portionwise with 450 ml