HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 24299
Notes
Print preview

Reaction equation

HRID 24299 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-eb8d8b4b51e54713ba1babd8bd6e5d5f
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06855840B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes