반응 #450555

반응 방정식

p-toluenesulfonyl chloride

1,4,7-triazaheptane

H2O

→

product

수율 93.0%

1,4,7-Tris(p-toluenesulfonyl)-1,4,7-triazaheptane

수율 93.0%

용매

pyridine

pyridine

반응 조건

후처리

1. 1
   기타This compound was synthesized
2. 2
   온도maintaining the temperature ≤50° C
3. 3
   workup.ADDITIONThe addition required 30 minutes
4. 4
   온도cooled (ice bath) mixture
5. 5
   기타The heavy white precipitate which formed
6. 6
   여과was filtered
7. 7
   세척washed thoroughly with H2O
8. 8
   workup.DISSOLUTIONThe pale yellow solid was dissolved in DMF (3 l)
9. 9
   workup.ADDITION0.1N HCl (4 l) was slowly added at 5° C
10. 10
    여과The slurry was filtered
11. 11
    세척the pale yellow solid was washed thoroughly with H2O
12. 12
    기타dried in vacuo

실험 절차

This compound was synthesized following the procedure of Atkins, T. J.; Richman, J. E.; and Oettle, W. F.; Org. synth., 58, 86-98 (1978). To a stirred solution of p-toluenesulfonyl chloride (618 g, 3.24 mole) in pyridine (1500 ml) at 0° C. was added a solution of 1,4,7-triazaheptane (95.5 g, 0.926 mole) in pyridine (150 ml) under a dry argon atmosphere, maintaining the temperature ≤50° C. The addition required 30 minutes. After the mixture was allowed to cool to room temperature slowly while stirring for 3 h, H2O (2 l) was slowly added to the cooled (ice bath) mixture. The heavy white precipitate which formed was filtered and washed thoroughly with H2O. The pale yellow solid was dissolved in DMF (3 l) and 0.1N HCl (4 l) was slowly added at 5° C. The slurry was filtered and the pale yellow solid was washed thoroughly with H2O and dried in vacuo to give 486 g (93% yield) of the product: mp 180°-1° C.; 1H NMR(DMSO-d6) δ 2.39 (s,3 H), 2.40 (s, 6 H), 2.84 (m, 4 H), 3.04 (t, J=6.9 Hz, 4 H) 7.40 (d, J=8.1 Hz, 4 H), 7.59 (d, J=8.3 Hz, 2 H), 7.67 (m, 6 H).

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