Potassium Carbonate → HCID 59536223, compound

HRID 454826Notes

Reaction equation

HRID 454826 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]([OH:18])[CH:15]=[CH:14][C:12]=3[CH:13]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[Si:25]([O:32][CH:33](Br)[CH3:34])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].[Cl-].[NH4+]>>[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][CH2:34][CH2:33][O:32][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH:15]=[CH:14][C:12]=3[CH:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 15142233HCID 15142233, compoundHCID 58160298HCID 58160298, compound

Product 1

HCID 59536223HCID 59536223, compoundYield 43%

Conditions

Temperature
80 °C

Procedure

2-[4-(N-Monomethylamino)phenyl]-6-hydroxybenzothiophene (113, 1.56 g, 4.52 mmol) and potassium carbonate (1.88 g, 13.57 mmol) were dissolved in dimethylacetimide (40 mL), 1-(t-butyldimethylsilyloxy)ethyl bromide (TBDMSO-CH2CH2Br) (114, 1.08 g, 4.52 mmol) was added thereto, and the reaction mixture was heated at 80° C. for 24 hours. To the reaction mixture was added an aqueous solution of ammonium chloride, and organic compounds were extracted with ethyl acetate. The recovered organic solvent was washed with a brine solution and dried over sodium sulfate. Purification was performed by column chromatography to give 2-[4-(N-monomethylamino)phenyl]-6-[2-(t-butyldimethylsilyloxy)ethoxy]benzothiophene (115, 804 mg, 43%) as a yellow solid. The obtained target compound 115 had a melting point of 118-119° C., and the following physical data;

Workup

  1. additionwas added
  2. extractionwere extracted with ethyl acetate
  3. washThe recovered organic solvent was washed with a brine solution
  4. dry with materialdried over sodium sulfate
  5. customPurification

Sources & evidence

ORD record
ord-3f0e27a7544a4f368f00e4cb382b2eaa
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

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