Ethanol → 4-(Ethylamino)butane-1-sulfonic acid

HRID 239797

Reaction equation

HRID 239797 reaction equation
[CH2:1]1[CH2:8][O:7][S:4](=[O:6])(=[O:5])[CH2:3][CH2:2]1.[CH2:9]([NH2:11])[CH3:10].CCO>O1CCCC1.CC(C)=O.CCO>[CH2:9]([NH:11][CH2:8][CH2:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5])[CH3:10]

Participants

6

Reactant 3

HCID 702EthanolHCID 6341EthylamineHCID 154111,4-Butane sultone

Product 1

HCID 190770254-(Ethylamino)butane-1-sulfonic acidYield 75%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21889777Acetone ethanolSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 1,4-butanesultone (2.66 g, 18.6 mmol) in tetrahydrofuran (total volume: 4 mL) was added via syringe pump over a 4 hour period to ethylamine (70% w/w in water, 24 mL, 372 mmol) at 5° C. The solution was stirred at 5° C. for an additional 3 hours before it was warm up to room temperature. The reaction was stirred in these conditions overnight. The solvent was coevaporated with EtOH (1×25 mL). The solid was suspended in 50% acetone/EtOH (50 mL). The suspension was stirred for 5 minutes, the solid was filtered and dried in vacuo. Yield: 75%. 1H NMR (D2O, 500 MHz) δ ppm 2.95 (m, 4H), 2.82 (m, 2H), 1.68 (m, 4H), 1.13 (t, 3H, J=7.3 Hz), 1.14 (t, 3H, J=7.3 Hz). 13C (D2O, 125 MHz) δ ppm 50.27, 46.68, 42.99, 24.66, 21.48, 10.64. ES-MS182 (M+1).

Workup

  1. temperaturewas warm up to room temperature
  2. stirringThe reaction was stirred in these conditions overnight
  3. stirringThe suspension was stirred for 5 minutes
  4. filtrationthe solid was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8817731986a14666811e1db0915318f8
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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