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

HRID 605289Notes

Reaction equation

HRID 605289 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-bd57b1622be445fcb574be2ec28d0f8d
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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