Imidazole → N-1H-Inden-3-ylacetamide

HRID 1582778Notes

Reaction equation

HRID 1582778 reaction equation
[C:1]1(=[N:10]O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.N1C=CN=C1.[C:17](OC(=O)C)(=[O:19])[CH3:18].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Ti+3]>[C:17]([NH:10][C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]=1)(=[O:19])[CH3:18]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 7918Acetic Anhydride2×HCID 10340Sodium CarbonateHCID 3023232,3-Dihydro-1H-inden-1-one oxime

Product 1

HCID 10130185N-1H-Inden-3-ylacetamideYield 61.3%

Reagents, catalysts & solvents 2

HCID 14117218HCID 14117218, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

1-Indanone oxime (2.33 g, 0.016 moles) and imidazole (78 mg) in acetonitrile (45 ml) cooled in ice, were treated with acetic anhydride (11 ml, 0.12 moles) and the mixture thus stirred for one hour. Titanium triacetate (17 g) was added, followed by more acetic anhydride (11 ml, 0.12 moles). The mixture was brought to reflux under nitrogen. After 2 hours the mixture was allowed to cool, poured into 1M sodium carbonate (250 ml) and stirred for 15 minutes. Three-fold extraction with ethyl acetate, drying (MgSO4) and evaporation left a brown oil which was reevaporated with toluene. The brown residue was subjected to flash chromatography on silica gel with ethyl acetate/hexane 1:2 v/v. The major component was obtained as a white solid (1.7 g) from the appropriate fractions and was recrystallized from ethyl acetate/hexane to give the title compound, mp 137-138° C. (1.45 g, 52.9%).

Workup

  1. temperatureto reflux under nitrogen
  2. waitAfter 2 hours the mixture was allowed
  3. temperatureto cool
  4. stirringstirred for 15 minutes
  5. extractionThree-fold extraction with ethyl acetate
  6. customdrying
  7. custom(MgSO4) and evaporation
  8. waitleft a brown oil which
  9. customwas reevaporated with toluene

Sources & evidence

ORD record
ord-d94c586946924f86bae69c005a79c13c
Source dataset
uspto-grants-2004_05
Patent number
US06737547B1

Reaction notes

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