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

HRID 507941Notes

Reaction equation

HRID 507941 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b230d8947a044238b04767200c3be560
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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