Hydrochloric Acid → 4'-(1-Cyclopentylethylamino)-2-(phenylsulfonyl)acetophenone

HRID 128326

Reaktionsgleichung

Reaktionsgleichung von HRID 128326
[H-].[Na+].[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].[CH:13]1([CH:18]([NH:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2C(OC)=O)[CH3:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.Cl.[O:32]1CCC[CH2:33]1>COCCOC>[CH:13]1([CH:18]([NH:20][C:21]2[CH:22]=[CH:27][C:28]([C:33](=[O:32])[CH2:3][S:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)(=[O:6])=[O:5])=[CH:29][CH:30]=2)[CH3:19])[CH2:14][CH2:15][CH2:16][CH2:17]1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 18369Methyl phenyl sulfoneHCID 24758Sodium hydrideHCID 54103355Methyl (1-cyclopentylethylamino)benzoate

Produkt 1

HCID 204990124'-(1-Cyclopentylethylamino)-2-(phenylsulfonyl)acetophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of 864 mg. of sodium hydride and 5.3 g. of methylphenylsulfone in 20 ml. of 1,2-dimethoxyethane is stirred at 6° C. for one hour under an atmosphere of argon. To this solution is added a solution of 5.0 g. of methyl (1-cyclopentylethylamino)benzoate in 50 ml. of tetrahydrofuran and the reaction mixture is stirred at 60° C. for 1.5 hours. The mixture is cooled, poured onto ice, acidified with dilute hydrochloric acid and pH 3 and then extracted with chloroform. The organic layer is separated, washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated to dryness. The crude solid is chromatographed on silica gel, eluting with methylene chloride to yield 4'-(1cyclopentylethylamino)-2-(phenylsulfonyl)acetophenone.

Aufarbeitung

  1. additionTo this solution is added a solution of 5.0 g
  2. temperatureThe mixture is cooled
  3. additionpoured onto ice
  4. extractionextracted with chloroform
  5. customThe organic layer is separated
  6. washwashed with water and saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated to dryness
  9. customThe crude solid is chromatographed on silica gel
  10. washeluting with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-5d91c82e3b2d43059a90c136a85010c3
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04259352

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