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Methyl iodide → (S)-Glycidyl N-methyl-N-Methanesulfonyl-p-Aminophenyl Ether

HRID 2223430
Notes
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Reaction equation

HRID 2223430 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C@H:14]2[O:16][CH2:15]2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[C:17](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:17][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][C@H:14]2[O:16][CH2:15]2)=[CH:10][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11322479(S)-N-(4-(Oxiran-2-ylmethoxy)phenyl)methanesulfonamide

Product 1

HCID 86593513(S)-Glycidyl N-methyl-N-Methanesulfonyl-p-Aminophenyl EtherYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of compound 3-S (0.243 g, 1 mmol) and potassium carbonate (0.166 g, 1.2 mmol) in 20 ml acetone was stirred for 1 hour at room temperature, then methyl iodide (0.142 g, 0.062 ml, 1 mmol) was added dropwise at room temperature. After stirring for 8 hours, the reaction was filtered and the solvent evaporated to furnish a white solid that was used directly in the next step (0.2 g, 78% yield).

Workup

  1. filtrationthe reaction was filtered
  2. customthe solvent evaporated
  3. customto furnish a white solid that

Sources & evidence

ORD record
ord-5355fc12a8214739a0cfcad600625718
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07375136B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes