Sodium Hydroxide → HCID 66935259, compound

HRID 554816Notes

Reaction equation

HRID 554816 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][SH:10])=[CH:5][CH:4]=1.[H-].[Na+].[CH3:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=1)=[O:16].[OH-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C:20]2[CH:21]=[CH:22][C:17]([C:15](=[O:16])[CH2:14][CH3:13])=[CH:18][CH:19]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 680044-FluoropropiophenoneHCID 804074-Methoxy-alpha-toluenethiol

Product 1

HCID 66935259HCID 66935259, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (4-methoxyphenyl)methane thiol (20 g) in N,N-dimethylformamide (200 ml) solution, sodium hydride (60% mineral oil dispersion) was added under ice cooling and the mixture was stirred for 10 minutes. 4-fluoropropiophenone was added to the reaction solution and the mixture was stirred at room temperature for 3 hours. 1N sodium hydroxide aqueous solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over with anhydrous sodium sulfate, then concentrated. Methanol was added to the residue, and the precipitated solid was collected by filtration to obtain the title compound (37.4 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionMethanol was added to the residue
  7. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-015a63b5aaaf42c3ab191bde78a67d36
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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