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

HRID 12602

Reaktionsgleichung

Reaktionsgleichung von HRID 12602
[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]

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24462Copper SulfateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-bcbee99499544c32b5f10b72d55104b4
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728022B2

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