HCID 67547885, compound → HCID 86593200, compound

HRID 2356738Notes

Reaction equation

HRID 2356738 reaction equation
Cl.Cl.[OH:3][CH2:4][C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:10]1[NH:11][C:12]([CH2:21][CH3:22])=[C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[N:14]=1>O1CCCC1.[O-2].[Mn+2]>[CH:4]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:10]1[NH:11][C:12]([CH2:21][CH3:22])=[C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[N:14]=1)=[O:3]

Participants

4

Reactant 1

HCID 67547885HCID 67547885, compound

Product 1

HCID 86593200HCID 86593200, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(2-hydroxymethylthiophen-3-yl)-5-ethyl-4-(3-pyridyl)imidazole dihydrochloride (212 mg) and manganese oxide (2 g) in tetrahydrofuran (15 ml) was refluxed for one hour. The reaction mixture was filtered and washed with tetrahydrofuran, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent: chloroform:methanol=30:1→20:1) to obtain 2-(2-formylthiophen-3-yl)-5-ethyl-4-(3-pyridyl)imidazole (93 mg) as orange crystal.

Workup

  1. temperaturewas refluxed for one hour
  2. filtrationThe reaction mixture was filtered
  3. washwashed with tetrahydrofuran
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: chloroform:methanol=30:1→20:1)

Sources & evidence

ORD record
ord-c7eae3a4f6ea49c3839f6de41e2f5d0b
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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