Ethyl Acetate → (NE,R)-N-[1-(3-chloro-2-fluorophenyl)ethylidene]-2-methylpropane-2-sulfinamide

HRID 930413

반응식

HRID 930413 반응식
[Cl:1][C:2]1[C:3]([F:11])=[C:4]([C:8](=O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH3:12][C:13]([S@:16]([NH2:18])=[O:17])([CH3:15])[CH3:14].CCOC(C)=O.C([O-])(O)=O.[Na+]>C1COCC1.[Cl-].[Na+].O.C(O[Ti](OCC)(OCC)OCC)C>[Cl:1][C:2]1[C:3]([F:11])=[C:4](/[C:8](=[N:18]/[S@@:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17])/[CH3:9])[CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 111165311-(3-Chloro-2-fluorophenyl)ethan-1-one

생성물 1

HCID 89095029(NE,R)-N-[1-(3-chloro-2-fluorophenyl)ethylidene]-2-methylpropane-2-sulfinamide수율 96%

시약·촉매·용매 3

HCID 178477244HCID 178477244, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
70 °C

실험 절차

To a solution of 1-(3-chloro-2-fluorophenyl)ethanone (5.60 g, 31.5 mmol) and (R)-2-methylpropane-2-sulfinamide (5.72 g, 47.2 mmol) in THF (50.0 mL) was added tetraethoxytitanium (16.50 mL, 79 mmol) and the overall bright yellow solution was heated at 70° C. for overnight. The reaction was slightly cooled with ice-water bath, then was added EtOAc (50 mL), NaHCO3 (10 mL), and brine (10 mL). The slurry was filtered through a short path of Celite and the wet cake was washed with EtOAc. The resulted bright yellow solution was phase separated, and the organic layer was concentrated to afford the title compound (8.3 g, 30.1 mmol, 96% yield) as a light yellow oil. This material was used in the next step without purification. MS m/z=276.0 [M+H]+. Calculated for C12H15ClFNOS: 275.77.

후처리

  1. temperatureThe reaction was slightly cooled with ice-water bath
  2. filtrationThe slurry was filtered through a short path of Celite
  3. washthe wet cake was washed with EtOAc
  4. customseparated
  5. concentrationthe organic layer was concentrated

출처 및 근거

ORD 기록
ord-d619eefffc7e41c49d079b63da1b4f74
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296734B2

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