Ethylenediamine → p-Toluenesulfonamide, N,N'-ethylenebis-

HRID 742529Notes

Reaction equation

HRID 742529 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].C(=O)([O-])[O-].[Na+].[Na+].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>O>[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17]([NH:3][CH2:2][CH2:1][NH:4][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=2)(=[O:19])=[O:18])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium Carbonate

Product 1

HCID 95237p-Toluenesulfonamide, N,N'-ethylenebis-Yield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethylenediamine (18.0 g, 0.30 mol) and sodium carbonate (64.0 g, 0.60 mol) in 750 mL of deionized water was heated to 75 C. To the mixture was added p-toluenesulfonyl chloride (125.0 g, 0.66 mol) in 5 g portions over 45 min. Then the reaction was stirred at 75 C. for 15 hours. After the mixture was cooled to 25 C., the white precipitate was filtered, washed with water and dried in a vacuum desiccator at 1 mm to yield 1,4-bis(p-toluenesulfonyl)-1,4-diazabutane (100.1 g, 0.29 mol, 98%).

Workup

  1. temperaturewas heated to 75 C
  2. temperatureAfter the mixture was cooled to 25 C
  3. filtration, the white precipitate was filtered
  4. washwashed with water
  5. customdried in a vacuum desiccator at 1 mm

Sources & evidence

ORD record
ord-cf74317e324e4c8bb8496a2c571475f0
Source dataset
uspto-grants-1996_09
Patent number
US05554749

Reaction notes

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