Sodium hydride → HCID 11617608, compound

HRID 971318Notes

Reaction equation

HRID 971318 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:9])[CH2:5][CH2:6][CH2:7][OH:8].F[C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1>O1CCOCC1>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([NH:20][S:17]([C:14]2[CH:15]=[CH:16][C:11]([O:8][CH2:7][CH2:6][CH2:5][N:4]([CH3:9])[CH3:3])=[CH:12][CH:13]=2)(=[O:19])=[O:18])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 766463-(Dimethylamino)-1-propanolHCID 341407N-(4-Chlorophenyl)-4-fluorobenzenesulfonamide

Product 1

HCID 11617608HCID 11617608, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a suspention of NaH (100 mmol, 55-65% in oil) in dry dioxane (140 mL) was added 3-dimethylamino-1-propanol (11.90 mL, 100 mmol). The mixture was stirred 1 h at room temperature. A solution of 4-fluoro-N-(4-chlorophenyl)benzenesulfonamide (9.53 g, 33.35 mmol, preparation described in example 66) in dry dioxane (35 mL) was added. The resulting mixture was heated 24 h at 100° C. Solvents were evaporated. NH4Cl saturated solution in water (75 mL) was added and the desired product was extracted with three portions of ethyl acetate (3×100 mL). Combined organic phases were dried over magnesium sulfate before filtering and removal of solvent. The desired product, e.g. N-(4-chlorophenyl)-4-[3-(dimethylamino)propoxy]benzenesulfonamide was obtained as a colorless oil, in 96% 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 (75 mL) was added
  4. extractionthe desired product was extracted with three portions of ethyl acetate (3×100 mL)
  5. dry with materialCombined organic phases were dried over magnesium sulfate
  6. filtrationbefore filtering
  7. customremoval of solvent

Sources & evidence

ORD record
ord-0ef7538437534ad888844be74b5fe0f6
Source dataset
uspto-grants-2007_12
Patent number
US07312358B2

Reaction notes

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