2,5-Bis(trifluoromethyl)benzaldehyde → (NE)-N-[[2,5-bis(trifluoromethyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide

HRID 12602

反応式

HRID 12602 の反応式
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:4]=1[CH:5]=O.[C:17]([S:21]([NH2:23])=[O:22])([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl.O.[O-]S([O-])(=O)=O.[Cu+2]>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:4]=1/[CH:5]=[N:23]/[S:21]([C:17]([CH3:20])([CH3:19])[CH3:18])=[O:22]

参加物

6

反応物 2

HCID 27378072,5-Bis(trifluoromethyl)benzaldehydeHCID 3382465Tert-Butanesulfinamide

生成物 1

HCID 57987489(NE)-N-[[2,5-bis(trifluoromethyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide収率 91%

試薬・触媒・溶媒 3

HCID 24462Copper Sulfate触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 2,5-bis trifluoromethyl benzaldehyde (21.5 g, 88.8 mmol), tert butyl sulfinamide (16.1 g, 133 mmol) and anhydrous CuSO4 (16.5 g, 103 mmol) in DCM (94 ml) was stirred at room temperature for 16 hours and at reflux for 3 days. The fine suspension was diluted with water and extracted with DCM. The extracts were washed with water, dried (MgSO4) and evaporated in vacuo to an off white solid which was purified by chromatography (silica, 4-10% EtOAc/isohexane) to give the desired N-{(1E)-[2,5-bis(trifluoromethyl)phenyl]methylene}-2-methylpropane-2-sulfinamide as a white crystalline solid (14.8 g, 91%); 1H NMR δ (ppm)(CDCl3): 8.98 (1 H, d, J=1.8 Hz), 8.46 (1 H, s), 7.92-7.85 (2 H, m), 1.29 (9 H, s); m/z (ES+) 346 (MH+).

後処理

  1. temperatureat reflux for 3 days
  2. extractionextracted with DCM
  3. washThe extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo to an off white solid which
  6. customwas purified by chromatography (silica, 4-10% EtOAc/isohexane)

出典と根拠

ORDレコード
ord-bcbee99499544c32b5f10b72d55104b4
出典データセット
uspto-grants-2010_06
特許番号
US07728022B2

関連ノート

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