6-(Trifluoromethyl)pyridine-3-carboxaldehyde → (NE)-2-methyl-N-[[6-(trifluoromethyl)-3-pyridinyl]methylidene]propane-2-sulfinamide

HRID 1047591ノート

反応式

HRID 1047591 の反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][N:4]=1.[CH3:13][C:14]([S@@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>ClC(Cl)C.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:13][C:14]([S:17](/[N:19]=[CH:7]/[C:6]1[CH:5]=[N:4][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:10][CH:9]=1)=[O:18])([CH3:16])[CH3:15]

参加物

5

反応物 2

HCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

生成物 1

HCID 87094737(NE)-2-methyl-N-[[6-(trifluoromethyl)-3-pyridinyl]methylidene]propane-2-sulfinamide収率 107.4%

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 63651,1-Dichloroethane溶媒

反応条件

温度
50 °C

実験手順

To a solution of 6-(trifluoromethyl)nicotinaldehyde (45.0 g, 257 mmol) in dichloroethane (640 mL) were added (S)-(−)-2-methyl-2-propanesulfinamide (34.3 g, 283 mmol) and anhydrous copper(II) sulfate (82 g, 514 mmol). The mixture was stirred at 50° C. After 48 h, the mixture cooled to ambient temperature. The reaction mixture was filtered through Celite. The filtered cake was washed with dichloromethane and the filtrate was concentrated to give the title compound (76.8 g). MS 223.1 (M-tert-butyl+1)

後処理

  1. temperaturethe mixture cooled to ambient temperature
  2. filtrationThe reaction mixture was filtered through Celite
  3. washThe filtered cake was washed with dichloromethane
  4. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-ffb912e814464ba49802ab8d2beaca60
出典データセット
uspto-grants-2013_10
特許番号
US08569512B2

反応ノート

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