Toluene → 6-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]nicotinaldehyde

HRID 1294201Notes

Reaction equation

HRID 1294201 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#N)=[CH:17][N:16]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].C(OCC)(=[O:44])C>CCCCCC>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:44])=[CH:17][N:16]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 688845976-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]nicotinonitrile

Product 1

HCID 229307406-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]nicotinaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of 6-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]nicotinonitrile (5.45 g) and anhydrous toluene (150 mL) was dropwise added a solution (0.95 M, 41.0 mL) of diisobutylaluminum hydride in hexane at −78° C. The reaction mixture was allowed to warm to room temperature with stirring for 1.5 hrs. A saturated aqueous ammonium chloride solution (100 mL) was dropwise added to the mixture, and the mixture was further stirred at room temperature for 30 min. Ethyl acetate was added to the mixture and the mixture was stirred at room temperature for 30 min. Insoluble materials were filtered away. The filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (4.30 g, 78%) of 6-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]nicotinaldehyde from a fraction eluted with ethyl acetate-hexane (1:4, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 120-121° C.

Workup

  1. stirringthe mixture was further stirred at room temperature for 30 min
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. filtrationInsoluble materials were filtered away
  4. washThe filtrate was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-61e82ceef29e46eb8192f9c80cfcaf92
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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