Acetonitrile → HCID 178518863, compound

HRID 2221543Notes

Reaction equation

HRID 2221543 reaction equation
C([O:8][C:9]1[C:13]([CH2:14][CH2:15][C:16]2[N:17]=[CH:18][S:19][CH:20]=2)=[CH:12][N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:10]=1)C1C=CC=CC=1.C(#N)C.I[Si](C)(C)C>O>[C:21]1([N:11]2[CH:12]=[C:13]([CH2:14][CH2:15][C:16]3[N:17]=[CH:18][S:19][CH:20]=3)[C:9]([OH:8])=[N:10]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 85247Trimethylsilyl iodideHCID 69217575HCID 69217575, compound

Product 1

HCID 178518863HCID 178518863, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-[2-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)ethyl]-1,3-thiazole (1.24 g) and acetonitrile (50 mL) was added iodotrimethylsilane (2.04 g) at room temperature. After stirring the reaction mixture at room temperature for 15 hrs., water was added to 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 (1:2, v/v) to give 1-phenyl-4-[2-(1,3-thiazol-4-yl)ethyl]-1H-pyrazol-3-ol as colorless crystals (0.48 g, yield 52%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 152-153° C.

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 (1:2

Sources & evidence

ORD record
ord-f837dbc9621a44f791271ff4e616f012
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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