4-Toluenesulfonyl chloride → HCID 21568620, compound

HRID 1579537Notes

Reaction equation

HRID 1579537 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.[CH2:12]([NH:14][CH2:15][CH2:16][NH2:17])[CH3:13]>N1C=CC=CC=1>[CH2:12]([NH:14][CH2:15][CH2:16][NH:17][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH3:13]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 66071N-Ethylethylenediamine

Product 1

HCID 21568620HCID 21568620, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 95 grams of p-toluenesulfonyl chloride in 175 ml. of pyridine was added dropwise to a stirred solution of 135 grams of N-ethyl ethylenediamine in 250 ml. of pyridine cooled in an ice bath. After addition was completed, the mixture was stirred one-half hour at room temperature then heated in a steam bath for one-half hour. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate and extracted with sodium carbonate solution and water. After drying the ethyl acetate portion over magnesium sulfate, the solvent was removed in vacuo to obtain N-[2-(ethylamino)ethyl]-p-toluenesulfonamide as a viscous oil which crystallized on standing. Analytical sample prepared from ether-hexane melted at 50°-53°C.

Workup

  1. additionAfter addition
  2. temperaturethen heated in a steam bath for one-half hour
  3. customThe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. extractionextracted with sodium carbonate solution and water
  6. dry with materialAfter drying the ethyl acetate portion over magnesium sulfate
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-800fd0fd8c3c4232aece9e5457fe993e
Source dataset
uspto-grants-1976_01
Patent number
US03931218

Reaction notes

Loading…