Sodium Chloride → HCID 59536218, compound

HRID 454827Notes

Reaction equation

HRID 454827 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([O:18][CH2:19][CH2:20][O:21][Si](C(C)(C)C)(C)C)[CH:15]=[CH:14][C:12]=3[CH:13]=2)=[CH:5][CH:4]=1.[C:29](=O)([O-])[O-].[K+].[K+].IC.[Cl-].[Na+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([O:18][CH2:19][CH2:20][OH:21])[CH:15]=[CH:14][C:12]=3[CH:13]=2)=[CH:5][CH:4]=1)[CH3:29]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 59536223HCID 59536223, compound

Product 1

HCID 59536218HCID 59536218, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-[4-(N-Monomethylamino)phenyl]-6-[2-(t-butyldimethylsilyloxy)ethoxy]benzothiophene (115, 150 mg, 0.36 mmol) obtained in Example 56 was dissolved in dimethylformamide (5 mL) and potassium carbonate (75 mg, 0.54 mmol) and iodomethane (0.23 mL, 0.36 mmol). The reaction mixture was stirred at 80° C. for 12 hours and an aqueous solution of sodium chloride and water were added to the reaction mixture and organic compounds were extracted with dichloromethane and extracted with ethyl acetate. The recovered organic solution was washed with a brine solution and dried over sodium sulfate to remove water and the solvent was removed under reduced pressure. The resulting mixture was dissolved in tetrahydrofuran (5 mL) and tetrabutylammonium fluoride (TBAF) (143 mg, 0.54 mmol) was added and stirred at room temperature for 30 minutes. Water was added to the reaction mixture and organic compounds were extracted with ethyl acetate. The recovered organic solution was washed with a saturated aqueous solution of sodium chloride and dried over sodium sulfate to remove water. Purification was performed by column chromatography to give 2-[4-(N,N-dimethylamino)phenyl]-6-(2-hydroxyethoxy)benzothiophene (118, 96 mg, 85%) as a white solid. The obtained target compound 118 had a melting point of 205-206° C., and the following physical data;

Workup

  1. extractionwere extracted with dichloromethane
  2. extractionextracted with ethyl acetate
  3. washThe recovered organic solution was washed with a brine solution
  4. dry with materialdried over sodium sulfate
  5. customto remove water
  6. customthe solvent was removed under reduced pressure
  7. dissolutionThe resulting mixture was dissolved in tetrahydrofuran (5 mL)
  8. stirringstirred at room temperature for 30 minutes
  9. extractionwere extracted with ethyl acetate
  10. washThe recovered organic solution was washed with a saturated aqueous solution of sodium chloride
  11. dry with materialdried over sodium sulfate
  12. customto remove water
  13. customPurification

Sources & evidence

ORD record
ord-7dcfd0904bc2415183442064efb7e993
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

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