反应详情

N,N′-bis(2-hydroxyethyl)-ethylenediamine (Aldrich, 14.8 g, 100 mmol) and pyridine (Fluka, 200 mL) was stirred at 0° C. under nitrogen while a solution of toluene-4-sulfonyl chloride (Fluka, 77 g, 400 mmol) dissolved in pyridine (Fluka, 100 mL) was dropped into the solution over a period of 75 minutes. The temperature was slowly raised to room temperature and continued stiffed for 4 hours. Solution was poured into a mixture of ice (250 mL) and hydrochloric acid (concentrated, 250 mL) while stirring to afford a dark sticky oil. Solvents were removed by decantation, product crude washed with water, decanted and re-dissolved in methanol (250 mL). The resulting slurry was isolated by filtration and the crude product was re-dissolved in hot methanol (60° C., 600 mL) and cooled down. Solid product was filtered off and dried in vacuo. Yield 36.36 g (47.5%). Product was verified by NMR.

1. additionwas dropped into the solution over a period of 75 minutes
2. customto afford a dark sticky oil
3. customSolvents were removed by decantation, product crude
4. washwashed with water
5. customdecanted
6. dissolutionre-dissolved in methanol (250 mL)
7. customThe resulting slurry was isolated by filtration
8. temperaturecooled down
9. filtrationSolid product was filtered off
10. customdried in vacuo