Cesium carbonate → N-[5-(4-Hydroxy-phenylsulfanyl)-2-methyl-4-nitro-phenyl]-2-phenyl-acetamide

HRID 605289노트

반응식

HRID 605289 반응식
Cl[C:2]1[C:3]([N+:19]([O-:21])=[O:20])=[CH:4][C:5]([CH3:18])=[C:6]([NH:8][C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1.[SH:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[OH:29][C:26]1[CH:27]=[CH:28][C:23]([S:22][C:2]2[C:3]([N+:19]([O-:21])=[O:20])=[CH:4][C:5]([CH3:18])=[C:6]([NH:8][C:9](=[O:17])[CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:7]=2)=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 2401474-MercaptophenolHCID 2907847N-(5-chloro-2-methyl-4-nitrophenyl)-2-phenylacetamide

생성물 1

HCID 67041085N-[5-(4-Hydroxy-phenylsulfanyl)-2-methyl-4-nitro-phenyl]-2-phenyl-acetamide수율 72%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The product from Example 265A (0.305 g, 1.0 mmol), 4-mercaptophenol (0.151 g, 1.2 mmol, 1.2 eq) and cesium carbonate (0.782 g, 2.4 mmol, 2.4 eq) in dimethyl formamide (10 mL) was heated at 110° C. for 2 h, cooled to room temperature, and poured over ice water (100 mL). This mixture was extracted with ethyl acetate (3×150 mL) and the combined organic phases were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was purified by chromatography on silica gel eluting with 1:1 hexane/ethyl acetate to provide the title compound as a yellow solid (0.282 g, 72%).

후처리

  1. extractionThis mixture was extracted with ethyl acetate (3×150 mL)
  2. washthe combined organic phases were washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel eluting with 1:1 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-bd57b1622be445fcb574be2ec28d0f8d
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910595B2

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