Potassium Carbonate → HCID 12628076, compound

HRID 1746685Notes

Reaction equation

HRID 1746685 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 158094-NitrobenzenethiolHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 12628076HCID 12628076, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-nitrobenzenethiol (Aldrich, 2.5 g; 16.1 mmol) in acetone (110 ml) was treated with potassium carbonate (2.22 g; 16.1 mmol) and ethyl 4-bromobutanoate (Aldrich, 3.43 g; 17.6 mmol). After stirring at RT for 18 hours, the mixture was 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 (4.0 g, 92%).

Workup

  1. filtrationthe mixture was filtered
  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-756a1ea8b8394da692eb8320785e92fd
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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