2-Methoxyethanol → HCID 33800493, compound

HRID 971313Notes

Reaction equation

HRID 971313 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][OH:7].F[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1>O1CCOCC1>[CH3:3][O:4][CH2:5][CH2:6][O:7][C:9]1[CH:10]=[CH:11][C:12]([S:15]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)(=[O:16])=[O:17])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 7110724-Fluoro-N-(4-methylphenyl)benzenesulfonamide

Product 1

HCID 33800493HCID 33800493, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a suspention of NaH (2.2 mmol, 55-65% in oil) in dry dioxane (6 mL) was added 2-methoxyethanol (158 μl, 2 mmol). The mixture was stirred 1 h at room temperature. A solution of 4-fluoro-N-(4-methylphenyl)benzenesulfonamide (265.3 mg, 1 mmol) in dry dioxane (2 mL) was added. The resulting mixture was heated 24 h at 100° C. Solvents were evaporated. NH4Cl saturated solution in water (5 mL) was added and the desired product was extracted with three portions of ethyl acetate (3×5 mL). Combined organic phases were dried over magnesium sulfate before filtering and removal of solvent. The desired product, e.g. 4-(2-methoxyethoxy)-N-(4-methylphenyl)benzenesulfonamide was obtained as a colorless oil, in 77% purity by HPLC (MaxPlot detection between 230 and 400 nm). This intermediate was used in the next step without further purification.

Workup

  1. temperatureThe resulting mixture was heated 24 h at 100° C
  2. customSolvents were evaporated
  3. additionNH4Cl saturated solution in water (5 mL) was added
  4. extractionthe desired product was extracted with three portions of ethyl acetate (3×5 mL)
  5. dry with materialCombined organic phases were dried over magnesium sulfate
  6. filtrationbefore filtering
  7. customremoval of solvent

Sources & evidence

ORD record
ord-43a46197b8484fecbe3a92d969eba136
Source dataset
uspto-grants-2007_12
Patent number
US07312358B2

Reaction notes

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