2,4-Bis(trifluoromethyl)benzaldehyde → (NE)-N-[[2,4-bis(trifluoromethyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide

HRID 12601

Reaktionsgleichung

Reaktionsgleichung von HRID 12601
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[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]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[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 27360952,4-Bis(trifluoromethyl)benzaldehydeHCID 3382465Tert-Butanesulfinamide

Produkt 1

HCID 178455562(NE)-N-[[2,4-bis(trifluoromethyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24462Copper SulfateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2,4-bis trifluoromethyl benzaldehyde (10.0 g, 41.3 mmol), tert butyl sulfinamide (4.5 g, 37.2 mmol) and anhydrous CuSO4 (13.1 g, 82.6 mmol) in DCM (100 ml) was stirred at room temperature overnight. The fine suspension was diluted with water and extracted with DCM. The extracts were washed with water, dried (MgSO4) and evaporated in vacuo to afford the desired N-{(1E)-[2,4-bis(trifluoro methyl)phenyl]methylene}-2-methylpropane-2-sulfinamide as an off white solid (7.62 g, 53%), with no further purification. 1H NMR δ (ppm)(CDCl3): 8.99 (1 H, d, J=1.9 Hz), 8.35 (1 H, d, J=8.2 Hz), 8.02 (1 H, s), 7.92 (1 H, d, J=8.2 Hz), 1.28 (9 H, d, J=4.6 Hz); m/z (ES+) 346 (MH+).

Aufarbeitung

  1. extractionextracted with DCM
  2. washThe extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d8a15633b09740b3a83773b2d22693a7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728022B2

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