Reaktion #450555

Reaktionsgleichung

p-toluenesulfonyl chloride

1,4,7-triazaheptane

H2O

→

product

Ausbeute 93.0%

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

Ausbeute 93.0%

Lösungsmittel

pyridine

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis compound was synthesized
2. 2
   Temperaturmaintaining the temperature ≤50° C
3. 3
   workup.ADDITIONThe addition required 30 minutes
4. 4
   Temperaturcooled (ice bath) mixture
5. 5
   SonstigeThe heavy white precipitate which formed
6. 6
   Filtrationwas filtered
7. 7
   Waschenwashed 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
    FiltrationThe slurry was filtered
11. 11
    Waschenthe pale yellow solid was washed thoroughly with H2O
12. 12
    Sonstigedried in vacuo

Vorschrift

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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