Potassium Carbonate → HCID 59446985, compound

HRID 1946699Notes

Reaction equation

HRID 1946699 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[SH:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CC(C)=O>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][S:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:4][CH:5]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21625Ethyl 3-mercaptopropionateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 59446985HCID 59446985, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-(bromomethyl)-4-nitrobenzene (Aldrich, 3.8 g; 17.6 mmol) in acetone (100 ml) was treated with potassium carbonate (2.22 g; 15.9 mmol) and ethyl 3-mercaptopropanoate (Aldrich, 2.14 g; 15.9 mmol). After stirring at RT for 18 hours the mixture filtered and the solid washed with acetone. The organic fractions were combined and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of Et2O to give the title compound as an off-white solid (3.6 g, 84%).

Workup

  1. filtrationfiltered
  2. washthe solid washed with acetone
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by column chromatography (silica)
  5. washeluting with petroleum ether containing
  6. temperatureincreasing amounts of Et2O

Sources & evidence

ORD record
ord-1a0cefab49554f3ab551f06a03656523
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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