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

HRID 605289ノート

反応式

HRID 605289 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-bd57b1622be445fcb574be2ec28d0f8d
出典データセット
uspto-grants-2011_03
特許番号
US07910595B2

反応ノート

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