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

HRID 930413

反応式

HRID 930413 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178477244HCID 178477244、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d619eefffc7e41c49d079b63da1b4f74
出典データセット
uspto-grants-2016_03
特許番号
US09296734B2

関連ノート

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