Taurine → 2-({2-Hydroxy-3-[(prop-2-en-1-yl)oxy]propyl}amino)ethane-1-sulfonic acid

HRID 1105497Notes

Reaction equation

HRID 1105497 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5].[OH-].[Na+].C(OCCO)C.[CH2:16]([O:20][CH2:21][CH:22]=[CH2:23])[CH:17]1[O:19][CH2:18]1>N(C1C=CC(O)=CC=1)=O.O>[OH:19][CH:17]([CH2:16][O:20][CH2:21][CH:22]=[CH2:23])[CH2:18][NH:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5]

Participants

7

Reactant 4

HCID 1123TaurineHCID 7838Allyl glycidyl etherHCID 8076Glycol monoethyl etherHCID 14798Sodium Hydroxide

Product 1

HCID 221578832-({2-Hydroxy-3-[(prop-2-en-1-yl)oxy]propyl}amino)ethane-1-sulfonic acidYield 40.2%

Reagents, catalysts & solvents 2

HCID 77294-NitrosophenolCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Into a 2 liter volume flask equipped with a stirrer, taurine (125 g), sodium hydroxide (40 g), deionized water (200 g) and ethylene glycol monoethyl ether (600 g) were charged. The contents were maintained at 60° C. while stirring, and a mixture of allyl glycidyl ether (114 g) and p-nitrosophenol (0.1 g) was dropwise added thereto in 20 minutes. Thereafter, stirring was continued for 2 hours. The reaction mixture of pH 9 was treated with an ionic exchange resin (Amberlite IR-120) to eliminate Na+ ion, whereby a solution of pH 4 was obtained. The solution was concentrated in a rotary evaporator to make a 7/10 volume so that needle crystals were precipitated. These crystals were identified to unreacted taurine by NMR and IR. The filtrate was poured into a 3 time volume of acetone to precipitate brown oily materials. The oily materials were collected and dried in vacuo as give N-(2-hydroxy-3-allyloxypropyl)taurine (96 g) of the formula: ##STR7##

Workup

  1. customInto a 2 liter volume flask equipped with a stirrer
  2. additionwas dropwise added
  3. stirringThereafter, stirring
  4. waitwas continued for 2 hours
  5. additionThe reaction mixture of pH 9
  6. additionwas treated with an ionic exchange resin (Amberlite IR-120)
  7. customwas obtained
  8. concentrationThe solution was concentrated in a rotary evaporator
  9. customwere precipitated
  10. additionThe filtrate was poured into a 3 time volume of acetone
  11. customto precipitate brown oily materials
  12. customThe oily materials were collected
  13. customdried in vacuo

Sources & evidence

ORD record
ord-15fa9d8b4f7e4b179c3454555725b902
Source dataset
uspto-grants-1982_01
Patent number
US04309327

Reaction notes

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