Methyl morpholine oxide → HCID 57687738, compound

HRID 1670875Notes

Reaction equation

HRID 1670875 reaction equation
[C:1]1([N:7]2[CH:11]=[C:10]([CH2:12][OH:13])[N:9]=[C:8]2[S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])CCOCC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]1([N:7]2[CH:11]=[C:10]([CH:12]=[O:13])[N:9]=[C:8]2[S:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 57687714HCID 57687714, compound

Product 1

HCID 57687738HCID 57687738, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of [1-phenyl-2-(phenylthio)-1H-imidazol-4-yl]methanol (740 mg) in acetonitrile (50 mL) were added tetra-n-propylammonium perruthenate (185 mg), N-methylmorpholine N-oxide (1.42 g) and molecular sieves 4A powder (5 g), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=3:2) to give the title compound as a pale-yellow oil (yield 400 mg, 54%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=3:2)

Sources & evidence

ORD record
ord-63d395bc157b4a9ab636a0fa89cd37e6
Source dataset
uspto-grants-2011_08
Patent number
US07994205B2

Reaction notes

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