Ethyl Acetate → HCID 136146921, compound

HRID 1674134Notes

Reaction equation

HRID 1674134 reaction equation
O=[C:2]([CH3:15])[CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]([O:6]CC)=O.Cl.[C:17](=[NH:22])([NH2:21])[CH2:18][CH2:19][CH3:20].N12CCCN=C1CCCCC2.C(OCC)(=O)C>CN(C)C=O.O>[CH3:15][C:2]1[N:21]=[C:17]([CH2:18][CH2:19][CH3:20])[NH:22][C:4](=[O:6])[C:3]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 95389Ethyl acetylphenylacetateHCID 12828983Butanimidamide hydrochloride

Product 1

HCID 136146921HCID 136146921, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 3-oxo-2-phenylbutanoate (2.28 g) and butanimidamide hydrochloride (2.04 g) in N,N-dimethylformamide (30 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (5.0 mL), and the mixture was stirred at 100° C. for 15 hr. Ethyl acetate and water were added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow viscous substance (0.26 g, 10%).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a715ec8f58494811a2bca97f5e1fbbdf
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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