Sodium Chloride → HCID 68498600, compound

HRID 454828Notes

Reaction equation

HRID 454828 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]CCO[Si](C(C)(C)C)(C)C)[CH:15]=[CH:14][C:12]=3[CH:13]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[Si:35]([O:52][CH2:53][CH2:54][CH2:55]Br)([C:48]([CH3:51])([CH3:50])[CH3:49])([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[Cl-].[Na+]>>[CH3:1][NH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([O:18][CH2:55][CH2:54][CH2:53][O:52][Si:35]([C:48]([CH3:49])([CH3:51])[CH3:50])([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH:15]=[CH:14][C:12]=3[CH:13]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 11245865177338-13-5HCID 59536223HCID 59536223, compound

Product 1

HCID 68498600HCID 68498600, compoundYield 69.1%

Procedure

2-[4-(N-Monomethylamino)phenyl]-6-hydroxybenzothiophene (115, 150 mg, 0.59 mmol) and potassium carbonate (122 mg, 0.89 mmol) were dissolved in dimethylacetimide (10 mL), and 3-(t-butyldiphenylsilyloxy)propyl bromide (TBDMSO-CH2CH2CH2Br) (444 mg, 1.18 mmol) was added. The reaction mixture was reacted at 90° C. for 6 hours. To the reaction mixture was added an aqueous solution of sodium chloride and organic compounds were extracted with ethyl acetate. The recovered organic solution 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-[3-(t-butyldiphenylsilyloxy)propoxy]benzothiophene (120, 225 mg, 69%) as a yellow solid.

Workup

  1. additionwas added
  2. customThe reaction mixture was reacted at 90° C. for 6 hours
  3. extractionwere extracted with ethyl acetate
  4. washThe recovered organic solution was washed with a brine solution
  5. dry with materialdried over sodium sulfate
  6. customPurification

Sources & evidence

ORD record
ord-12548614fc4b40fe9e3d354328fccff7
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

Loading…