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

HRID 1683201Notes

Reaction equation

HRID 1683201 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][NH2:18].[OH2:19]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH:12][CH2:13][CH2:14][N:15]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:16][CH2:17][NH:18][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:8])=[O:19])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8111Diethylenetriamine

Product 1

HCID 316685N,N'-{[(4-Methylbenzene-1-sulfonyl)azanediyl]di(ethane-2,1-diyl)}bis(4-methylbenzene-1-sulfonamide)Yield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

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).

Workup

  1. customThis compound was synthesized
  2. temperaturemaintaining the temperature<50 C
  3. additionThe addition required 30 minutes
  4. temperaturecooled (ice bath) mixture
  5. customThe heavy white precipitate which formed
  6. filtrationwas filtered
  7. washwashed-thoroughly with H2O
  8. dissolutionThe pale yellow solid was dissolved in DMF (3 l)
  9. addition0.1N HCl (4 l) was slowly added at 5° C
  10. filtrationThe slurry was filtered
  11. washthe pale yellow solid was washed thoroughly with H2O
  12. customdried in vacuo

Sources & evidence

ORD record
ord-2566d187b587489595f51ff90ce4ea02
Source dataset
uspto-grants-1997_06
Patent number
US05637578

Reaction notes

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