Diisopropylethylamine → 1620-50-4

HRID 602816Notes

Reaction equation

HRID 602816 reaction equation
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.CCN(C(C)C)C(C)C.[C:19]1([S:25]([O-:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Na+]>CC#N>[C:19]1([S:25]([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=2)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2723840Benzenesulfinic acid, sodium saltHCID 27347202-(Bromomethyl)pyridine hydrobromide

Product 1

HCID 33210621620-50-4Yield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 2.5 g (0.010 mol) of 2-bromomethyl-pyridine hydrobromide in 10 mL of CH3CN at RT, was added 1.78 mL (0.0105 mol, 1.05 eq.) of Hunig's base. After complete dissolution of the salt, 1.62 g (0.010 mol, 1 eq.) of sodium benzene sulfinat and 0.52 g (0.002 mol, 0.2 eq.) were added. The mixture was stirred at RT for 48 hours, and then the reaction was quenched by addition of water, and the product extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and dried under vacuum to afford 1.86 g (80%) of 2-benzenesulfonylmethyl-pyridine.

Workup

  1. additionwere added
  2. customthe reaction was quenched by addition of water
  3. extractionthe product extracted with EtOAc
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ae23911d2ec3461a8c1a9515accbdc9e
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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