Hydrochloric Acid → Tetratosyl-N,N'-bis(2-hydroxyethyl)ethylene diamine

HRID 2174321Notes

Reaction equation

HRID 2174321 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][OH:10].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.Cl>N1C=CC=CC=1.CO>[S:17]([C:6]([S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18])([NH:7][CH2:8][CH2:9][OH:10])[C:5]([S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18])([S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18])[NH:4][CH2:3][CH2:2][OH:1])([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 78179Ethanol, 2,2'-(1,2-ethanediyldiimino)bis-

Product 1

HCID 89871954Tetratosyl-N,N'-bis(2-hydroxyethyl)ethylene diamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent2×

Procedure

N,N′-bis(2-hydroxyethyl)-ethylenediamine (Aldrich, 14.8 g, 100 mmol) and pyridine (Fluka, 200 mL) was stirred at 0° C. under nitrogen while a solution of toluene-4-sulfonyl chloride (Fluka, 77 g, 400 mmol) dissolved in pyridine (Fluka, 100 mL) was dropped into the solution over a period of 75 minutes. The temperature was slowly raised to room temperature and continued stiffed for 4 hours. Solution was poured into a mixture of ice (250 mL) and hydrochloric acid (concentrated, 250 mL) while stirring to afford a dark sticky oil. Solvents were removed by decantation, product crude washed with water, decanted and re-dissolved in methanol (250 mL). The resulting slurry was isolated by filtration and the crude product was re-dissolved in hot methanol (60° C., 600 mL) and cooled down. Solid product was filtered off and dried in vacuo. Yield 36.36 g (47.5%). Product was verified by NMR.

Workup

  1. additionwas dropped into the solution over a period of 75 minutes
  2. customto afford a dark sticky oil
  3. customSolvents were removed by decantation, product crude
  4. washwashed with water
  5. customdecanted
  6. dissolutionre-dissolved in methanol (250 mL)
  7. customThe resulting slurry was isolated by filtration
  8. temperaturecooled down
  9. filtrationSolid product was filtered off
  10. customdried in vacuo

Sources & evidence

ORD record
ord-b6e544e7ffc84e81be56d92a33e843c3
Source dataset
uspto-grants-2015_06
Patent number
US09061080B2

Reaction notes

Loading…