Taurine → Sodium 2-(2-bromopropionylamino)-ethanesulfonate

HRID 349601

Reaction equation

HRID 349601 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5].[OH-].[Na+:9].[Br:10][CH:11]([CH3:15])[C:12](Br)=[O:13]>O.ClCCl>[Br:10][CH:11]([CH3:15])[C:12]([NH:1][CH2:2][CH2:3][S:4]([O-:7])(=[O:6])=[O:5])=[O:13].[Na+:9]

Participants

6

Reactant 3

HCID 1123TaurineHCID 14798Sodium HydroxideHCID 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 23709737Sodium 2-(2-bromopropionylamino)-ethanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

25.6 g of taurine (204 mmol) and 16.38 g of NaOH (409 mmol) were dissolved in 20 ml of deionized water. 2-Bromopropionyl bromide (44 g, 21.36 ml, 204 mmol) dissolved in 50 ml of dichloromethane was then added to the solution drop wise at 0° C. over 30 minutes. During the addition, a large amount of solid was produced. The reaction flask was manually agitated to thoroughly mix the compounds until no more exotherm was observed with additional agitation. The reaction mixture was then allowed to sit for 1 hour. The solid was filtered and washed with a small amount of absolute ethanol and then ethyl ether and then dried in vacuo. The compound can be used in this state or recrystallized from methanol.

Workup

  1. additionwas then added to the solution drop wise at 0° C. over 30 minutes
  2. additionDuring the addition
  3. customa large amount of solid was produced
  4. additionto thoroughly mix the compounds until no more exotherm
  5. filtrationThe solid was filtered
  6. washwashed with a small amount of absolute ethanol
  7. dry with materialethyl ether and then dried in vacuo
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5c5a1cf74ab9419fa4b9b1eb01573707
Source dataset
uspto-grants-2007_02
Patent number
US07179872B2

Linked notes

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