1-(1H-Imidazol-1-yl)ethanone → HCID 86657028, compound

HRID 1047606Notes

Reaction equation

HRID 1047606 reaction equation
[CH2:1]([O:8][C:9](=[O:17])[NH:10][C@H:11]([CH3:16])/[C:12](/[NH2:15])=[N:13]/[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](N1C=CN=C1)(=O)[CH3:19]>O1CCOCC1>[CH2:1]([O:8][C:9](=[O:17])[NH:10][C@@H:11]([C:12]1[N:15]=[C:18]([CH3:19])[O:14][N:13]=1)[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 140555601HCID 140555601, compound

Product 1

HCID 86657028HCID 86657028, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of benzyl[(1R,2Z)-2-amino-2-(hydroxyimino)-1-methylethyl]carbamate (2.25 g, 9.48 mmol) in dioxane (80 ml) was added 1-acetyl-1H-imidazole (3.13 g, 28.5 mmol) and the mixture heated to 90° C. After 16 h, the solution was concentrated and the residue was dissolved in 200 mL of dichloromethane. The mixture was washed with 100 mL of aquous saturated sodium bicarbonate (2×) and saturated aqueous sodium chloride (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) to give the title compound (1.1 g). MS 262.1 (M+1).

Workup

  1. concentrationthe solution was concentrated
  2. dissolutionthe residue was dissolved in 200 mL of dichloromethane
  3. washThe mixture was washed with 100 mL of aquous saturated sodium bicarbonate (2×) and saturated aqueous sodium chloride (100 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

Sources & evidence

ORD record
ord-fa077f2bfbf848e1bef625f327a8d8dc
Source dataset
uspto-grants-2013_10
Patent number
US08569512B2

Reaction notes

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