Potassium Carbonate → N-(1-[5-[(4-ethoxybenzyl)sulfanyl]-1-benzofuran-2-yl]ethyl)acetamide

HRID 1888769노트

반응식

HRID 1888769 반응식
[SH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:7][C:6]=2[CH:16]=1.BrC1C=CC2OC(C(NC(=O)C)C)=CC=2C=1.[CH2:33]([O:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40]Cl)=[CH:38][CH:37]=1)[CH3:34].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[CH2:33]([O:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][S:1][C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8]([CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:7][C:6]=3[CH:16]=2)=[CH:38][CH:37]=1)[CH3:34]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 20639711-(Chloromethyl)-4-EthoxybenzeneHCID 58047276N-[1-(5-bromo-1-benzofuran-2-yl)ethyl]acetamideHCID 67015783N-[1-(5-sulfanyl-1-benzofuran-2-yl)ethyl]acetamide

생성물 1

HCID 58047107N-(1-[5-[(4-ethoxybenzyl)sulfanyl]-1-benzofuran-2-yl]ethyl)acetamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of the obtained mixture (750 mg) of N-[1-(5-sulfanyl-1-benzofuran-2-yl)ethyl]acetamide and N-[1-(5-bromo-1-benzofuran-2-yl)ethyl]acetamide in anhydrous DMF (6.4 mL) were added 4-ethoxybenzyl chloride (1.09 g, 6.38 mmol) and potassium carbonate (880 mg, 0.456 mmol), and the reaction mixture was stirred at room temperature overnight. Saturated brine was added thereto, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:4), and the obtained solid was washed with diethyl ether to give N-(1-{5-[(4-ethoxybenzyl)sulfanyl]-1-benzofuran-2-yl}ethyl)acetamide (205 mg, yield from (N-[1-(5-{[tert-butyl(dimethyl)silyl]oxy}-1-benzothiophen-2-yl)ethyl]acetamide 16%).

후처리

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:4)
  6. washthe obtained solid was washed with diethyl ether

출처 및 근거

ORD 기록
ord-cb0facc11a13449da16c70af8b020273
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501804B2

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