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

HRID 2287778Notes

Reaction equation

HRID 2287778 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 0.1 N 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. l Hz, 4 H), 7.59 (d, J=8.3 Hz, 2 H), 7.67 (m, 6 H).

Workup

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

Sources & evidence

ORD record
ord-3c76cfd47a604b96af5a0735fef49d6f
Source dataset
uspto-grants-2000_07
Patent number
US06084093

Reaction notes

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