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

HRID 12602

반응식

HRID 12602 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 24462Copper Sulfate촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-bcbee99499544c32b5f10b72d55104b4
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728022B2

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