p-(Trifluoromethoxy)benzaldehyde → (NE,R)-2-methyl-N-[[4-(trifluoromethoxy)phenyl]methylidene]propane-2-sulfinamide

HRID 57467

反応式

HRID 57467 の反応式
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[CH3:14][C:15]([S@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>ClCCCl.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:14][C:15]([S@:18](/[N:20]=[CH:8]/[C:7]1[CH:10]=[CH:11][C:4]([O:3][C:2]([F:13])([F:12])[F:1])=[CH:5][CH:6]=1)=[O:19])([CH3:17])[CH3:16]

参加物

5

反応物 2

HCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

生成物 1

HCID 90416044(NE,R)-2-methyl-N-[[4-(trifluoromethoxy)phenyl]methylidene]propane-2-sulfinamide収率 102.3%

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 111,2-Dichloroethane溶媒

反応条件

温度
55 °C

実験手順

To a cloudy solution of 4-(trifluoromethoxy)benzaldehyde (5 g, 26.3 mmol) and (R)-2-methylpropane-2-sulfinamide (3.51 g, 28.9 mmol) in DCE (52 mL), under N2, was added copper (II) sulfate (6.30 g, 39.4 mmol), and the resulting mixture heated in a preheated oil bath at 55° C. for 22 hours. The reaction mixture was filtered through a pad of celite, eluting with DCM. The filtrate was concentrated to afford a viscous yellow oil of (R,E)-2-methyl-N-(4-(trifluoromethoxy)benzylidene)propane-2-sulfinamide (7.9 g, 26.9 mmol, 102% yield). Material was taken onto next step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 1.27 (s, 9H) 7.32 (d, J=8.07 Hz, 2H) 7.91 (d, J=8.75 Hz, 2H) 8.59 (s, 1H). LCMS m/z 294.1 (M+H)+, Rt 1.01 min.

後処理

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washeluting with DCM
  3. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-a0ad5be0d3c242568b69b88b9d9f3d76
出典データセット
uspto-grants-2016_09
特許番号
US09434719B2

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