Water → N,N'-{[(4-Methylbenzene-1-sulfonyl)azanediyl]di(ethane-2,1-diyl)}bis(4-methylbenzene-1-sulfonamide)

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Reaction Steps

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) δ2.39 (s, 3H), 2.40 (s, 6H), 2.84 (m, 4H), 3.04 (t, J=6.9 Hz, 4H) 7.40 (d, J=8.1 Hz, 4H), 7.59 (d, J=8.3 Hz, 2H), 7.67 (m, 6H).

Provenance & Evidence