Acetic Acid → HCID 178441706, compound

HRID 2254603Notes

Reaction equation

HRID 2254603 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C-]#N.[Na+].C[C:17](O)=[O:18]>CO.O=[Mn]=O>[CH2:1]([C:5]1[NH:6][C:7]([C:11]([O:18][CH3:17])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 178418251HCID 178418251, compound

Product 1

HCID 178441706HCID 178441706, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-Butyl-4-chloro-5-formylimidazole (4.9 g, 26 mMol) in methanol (350 ml) were added NaCN (12.98 g, 0.26 Mol), glacial AcOH (2.5 ml) and MnO2 (57.6 g, 0.663 Mol), and the mixture was stirred at room temperature for 72 h. The reaction was filtered through a pad of celite and concentrated in vacuo. The residue obtained was partitioned between EtOAc (150 ml) and water (50 ml), and the organic phase was washed with brine and then dried over sodium sulfate. The crude product (5.73 g), obtained after removal of the solvent under reduced pressure, was purified by flash-chromatography on silica-gel using EtOAc-hexane (1:5). Yield 4.5 g (80%, white solid). The product was crystallized from ethylacetate-hexane to give fine needles.

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. customThe residue obtained
  4. customwas partitioned between EtOAc (150 ml) and water (50 ml)
  5. washthe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-ad9575b284c64b679572f4effc68f6d8
Source dataset
uspto-grants-1993_08
Patent number
US05236928

Reaction notes

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