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Ethanolamine → 1,1,1-trifluoro-N-(2-hydroxyethyl)methanesulfonamide

HRID 377398
Notes
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Reaction equation

HRID 377398 reaction equation
O.[OH-].[Na+].[NH2:4][CH2:5][CH2:6][OH:7].[F:8][C:9]([F:15])([F:14])[S:10](Cl)(=[O:12])=[O:11]>CC(C)=O>[F:8][C:9]([F:15])([F:14])[S:10]([NH:4][CH2:5][CH2:6][OH:7])(=[O:12])=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 700EthanolamineHCID 962WaterHCID 14798Sodium HydroxideHCID 79000Trifluoromethanesulfonyl chloride

Product 1

HCID 193587601,1,1-trifluoro-N-(2-hydroxyethyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a mixed solvent prepared from 100 ml of water and 50 ml of acetone and containing 3.2 g of sodium hydroxide, 3.7 g of 2-aminoethanol was reacted with 12.5 g of trifluoromethanesulfonyl chloride at room temperature for 12 hours. The solvent was evaporated from the resultant reaction mixture by vacuum distillation. To the residue was added 50 ml of chloroform. The sodium chloride generated was removed by filtration. The resultant chloroform solution was distilled under vacuum to obtain 2-trifluoromethanesulfonamidoethanol. A 10 g portion was taken out of this reaction product and dissolved in 100 ml of acetone. Thereto was added dropwise 12.0 g of thionyl chloride over a period of 3 minutes. Subsequently, 10 ml of an aqueous solution containing 2.06 g of sodium hydroxide was added thereto dropwise to react the reactants at 55° C. for 12 hours. The solvent was removed from the resultant reaction mixture, and 100 ml of water was added to the residue. After this mixture was stirred, 100 ml of diethyl ether was added to conduct extraction.

Workup

  1. customThe solvent was evaporated from the resultant
  2. customreaction mixture
  3. distillationby vacuum distillation
  4. additionTo the residue was added 50 ml of chloroform
  5. customThe sodium chloride generated was removed by filtration
  6. distillationThe resultant chloroform solution was distilled under vacuum

Sources & evidence

ORD record
ord-68a5c74181014b4684328d71dab5a485
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06025457

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes