Potassium Hydroxide → 1-(2,6-Dimethyl-4-(pyrazin-2-ylthio)phenyl)ethanone

HRID 1465540Notes

Reaction equation

HRID 1465540 reaction equation
O[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1.[N:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[SH:19].[OH-].[K+]>CN(C=O)C.O.[Cu-]=O>[CH3:8][C:6]1[CH:7]=[C:2]([S:19][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][N:13]=2)[CH:3]=[C:4]([CH3:12])[C:5]=1[C:9](=[O:11])[CH3:10]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 40573701-(4-Hydroxy-2,6-dimethylphenyl)ethanoneHCID 178527737HCID 178527737, compound

Product 1

HCID 866908421-(2,6-Dimethyl-4-(pyrazin-2-ylthio)phenyl)ethanoneYield 25%

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-iodo-2,6-dimethylphenyl)ethanone (4-2, 3.20 g, 11.7 mmol), pyrazine-2-thiol (11-1, 1.96 g, 17.5 mmol), copper(I) oxide (83.5 mg, 0.6 mmol), and potassium hydroxide (1.64 g, 29.2 mmol) in DMF (9.6 mL) and H2O (2.4 mL) was heated at reflux for 24 h. The mixture was quenched with H2O (10 mL) and extracted with ether (2×50 mL). The organic layer was collected, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (3.0% EtOAc in hexanes as eluant) to provide 1-(2,6-dimethyl-4-(pyrazin-2-ylthio)phenyl)ethanone (11-3, 755.2 mg) as yellow oil in 25% yield: 1H NMR (500 MHz, CDCl3) δ 8.47 (s, 1 H), 8.27 (s, 1 H), 8.22 (s, 1 H), 7.28 (s, 2 H), 2.51 (s, 3 H), 2.28 (s, 6 H); ESI-MS: m/z 259.3 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. customThe mixture was quenched with H2O (10 mL)
  4. extractionextracted with ether (2×50 mL)
  5. customThe organic layer was collected
  6. dry with materialdried over MgSO4(s)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (3.0% EtOAc in hexanes as eluant)

Sources & evidence

ORD record
ord-533711d0e59c439e8139fe30a76707b4
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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