Dimethylformamide → 4-{(Z)-2-[3-(benzyloxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-thiazole

HRID 2221541Notes

Reaction equation

HRID 2221541 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([CH:14]=O)=[CH:12][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[S:23]1[CH:27]=[C:26]([CH2:28][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:25]=[CH:24]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:1]([O:8][C:9]1[C:13](/[CH:14]=[CH:28]\[C:26]2[N:25]=[CH:24][S:23][CH:27]=2)=[CH:12][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 22175328Triphenyl(1,3-thiazol-4-ylmethyl)phosphonium chlorideHCID 229307603-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 692156044-{(Z)-2-[3-(benzyloxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-thiazoleYield 37.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehyde (1.70 g), [(1,3-thiazol-4-yl)methyl]triphenylphosphonium chloride (3.64 g), potassium carbonate (1.27 g) and N,N-dimethylformamide (100 mL) was stirred at room temperature for 15 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:3, v/v) to give 4-{(Z)-2-[3-(benzyloxy)-1-phenyl-1H-pyrazol-4-yl]ethenyl}-1,3-thiazole as a colorless oil (0.82 g, yield 37%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-hexane (1:3

Sources & evidence

ORD record
ord-f16cf242e6eb43789f45bbf76b536ad0
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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