Sodium Sulfide → 2-phenyl-6-(1-phenyl-1H-pyrazol-5-yl)-4H-thiopyran-4-one

HRID 1747828Notes

Reaction equation

HRID 1747828 reaction equation
[S-2:1].[Na+].[Na+].[O-]CC.[Na+].[C:8]1([C:14]#[C:15][C:16](=[O:30])[C:17]#[C:18][C:19]2[N:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:22]=[CH:21][CH:20]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)C>[C:8]1([C:14]2[S:1][C:18]([C:19]3[N:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:22]=[CH:21][CH:20]=3)=[CH:17][C:16](=[O:30])[CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 14804Sodium SulfideHCID 2723922Sodium ethoxideHCID 895861451-phenyl-5-(1-phenyl-1H-pyrazol-5-yl)penta-1,4-diyn-3-one

Product 1

HCID 680147852-phenyl-6-(1-phenyl-1H-pyrazol-5-yl)-4H-thiopyran-4-oneYield 28.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To sodium sulfide (0.079 g) was added 0.25 M sodium ethoxide in ethanol solution (20.0 mL), and the mixture was stirred at room temperature for 10 min. To a solution of 1-phenyl-5-(1-phenyl-1H-pyrazol-5-yl)penta-1,4-diyn-3-one (0.25 g) in ethanol (10.0 mL) was added the above-mentioned solution, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol) to give the title compound (80.0 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-43bb6ee349ff40d3b3c2c6612a4533bd
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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