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

HRID 128326

반응식

HRID 128326 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5d91c82e3b2d43059a90c136a85010c3
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04259352

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