Sodium Iodide → 4-Isobutoxy-3-{[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}benzaldehyde

HRID 507941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507941
[C:1]1([C:7]2[N:8]=[C:9]([NH:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[O:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH:28]=[O:29].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH2:34]([O:33][C:32]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][C:25]=1[CH2:24][N:12]([CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[S:10][CH:11]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=1)[CH:35]([CH3:37])[CH3:36]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 543394-Phenyl-N-(2-phenylethyl)-2-thiazolamineHCID 231573903-(Chloromethyl)-4-isobutoxybenzaldehyde

Produkt 1

HCID 231574914-Isobutoxy-3-{[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}benzaldehydeAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-phenyl-N-(2-phenylethyl)-1,3-thiazole-2-amine (0.95 g, 3.40 mmol) in N,N-dimethylformamide (7 mL) was added sodium hydride (60% in oil, 0.14 g, 3.40 mmol) under stirring at 0° C., and the mixture was stirred at the same temperature for 5 min. Then, 3-(chloromethyl)-4-isobutoxybenzaldehyde (0.70 g, 3.09 mmol) and sodium iodide (0.51 g, 3.40 mmol) were added to the reaction mixture, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-3/1) to give the title compound (1.43 g, yield 99%) as a pale-yellow oil.

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 5 min
  2. stirringthe mixture was stirred at room temperature for 16 hr
  3. washwashed with water and saturated brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-3/1)

Quellen und Nachweise

ORD-Eintrag
ord-b230d8947a044238b04767200c3be560
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786165B2

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