Dimethyl Sulfoxide → HCID 69423196, compound

HRID 349908Notes

Reaction equation

HRID 349908 reaction equation
I[CH2:2][CH2:3][CH2:4][C:5]1[C:6]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:7][N:8]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[N:20]=[C:21]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[O:22][C:23]=3[CH3:24])=[CH:13][CH:12]=2)[CH:9]=1.[C-:37]#[N:38].[Na+].CS(C)=O>O>[CH3:24][C:23]1[O:22][C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:20][C:19]=1[CH2:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:8]2[CH:9]=[C:5]([CH2:4][CH2:3][CH2:2][C:37]#[N:38])[C:6]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[N:7]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 23024979HCID 23024979, compound

Product 1

HCID 69423196HCID 69423196, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-iodo-3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-phenyl-1H-pyrazol-4-yl]propane (1.75 g), sodium cyanide (291 mg), and dimethyl sulfoxide (5 ml) was stirred at 60° C. for 2 hours. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and 4-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-phenyl-1H-pyrazol-4-yl]butyronitrile (1.34 g, yield: 92%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (2:3, volume ratio).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f69e0e35bffe4b288631e4a987f9b3ee
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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