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Water → 6-[(Methylsulfonyl)methyl]pyridin-3-yl benzenesulfonate

HRID 1042114
Notes
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Reaction equation

HRID 1042114 reaction equation
[C:1]1([S:7]([O:10][C:11]2[CH:12]=[N:13][C:14]([CH2:17]Br)=[CH:15][CH:16]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][S:20]([O-:22])=[O:21].[Na+].O>CN(C)C=O>[C:1]1([S:7]([O:10][C:11]2[CH:12]=[N:13][C:14]([CH2:17][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:15][CH:16]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 2733271Sodium methanesulfinateHCID 10639974HCID 10639974, compound

Product 1

HCID 866618286-[(Methylsulfonyl)methyl]pyridin-3-yl benzenesulfonateYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(bromomethyl)pyridin-3-yl benzenesulfonate (30 g) in N,N-dimethylformamide (200 mL) was added sodium methylsulfinate (11.2 g), and the mixture was stirred at room temperature for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (30 g, yield 100%) as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4f5d37a94074eaf8b44ac0bba5a8da3
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08557805B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes