Potassium Carbonate → 1-(5-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophen-2-yl)ethanone

HRID 1192041Notes

Reaction equation

HRID 1192041 reaction equation
Cl[C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[Na].[Cl:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([Cl:22])[C:20]=1[SH:21].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([Cl:22])[C:20]=1[S:21][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5211051-(5-Chloro-4-nitrothiophen-2-yl)ethan-1-oneHCID 178527724HCID 178527724, compound

Product 1

HCID 469320561-(5-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophen-2-yl)ethanoneYield 12%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(5-chloro-4-nitro-2-thienyl)ethanone (113 mg, 0.55 mmol) in toluene (2 mL), was added 3,5-dichloropyridine-4-thiol sodium salt (100 mg, 0.55 mmol) and potassium carbonate (113 mg, 0.825 mmol). The resulting reaction mixture was stirred at ambient temperature for 18 hours. After this time, the reaction mixture was filtered to remove the solid residues. The organic solution was diluted with ethyl acetate (15 mL) and was washed with water (2 mL×2) and brine (1 mL×2), dried (Na2SO4) and concentrated under vacuum. The residue was purified by silica gel chromatography using a mixture of 96:4 hexane and ethyl acetate as eluent to afford the title product as a solid (22 mg, 12% yield). 1H NMR (400 MHz, MeOD) δ: 8.85 (2H, m) 8.36 (1H, s), 2.52 (3H, s). MS m/z: 348.8 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. filtrationAfter this time, the reaction mixture was filtered
  3. customto remove the solid residues
  4. additionThe organic solution was diluted with ethyl acetate (15 mL)
  5. washwas washed with water (2 mL×2) and brine (1 mL×2)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by silica gel chromatography
  9. additiona mixture of 96:4 hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-1c96cdece2df4049830ca738970d1d3f
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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