Ethyl 3-oxo-3-(thiophen-2-yl)propanoate → HCID 136044398, compound

HRID 1091542Notes

Reaction equation

HRID 1091542 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8].C(O[C:16](=O)[CH2:17][C:18](=[O:24])[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)C>C1(C)C=CC=CC=1>[N:1]1[CH:5]=[CH:4][N:3]2[C:2]=1[C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[N:8]=[C:16]2/[CH:17]=[C:18](/[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)\[OH:24]

Participants

4

Reactant 2

HCID 255159Ethyl 3-oxo-3-(thiophen-2-yl)propanoateHCID 156205002-(1H-Imidazol-2-yl)aniline

Product 1

HCID 136044398HCID 136044398, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(1H-imidazol-2-yl)aniline (60.0 mg, 0.38 mmol), ethyl3-oxo-3-(2-thienyl)propanoate (74.7 mg, 0.38 mmol) and p-tolenesulfonicacid monohydrate (36.1 mg, 0.19 mmol) in toluene (30 ml) was heated at reflux for 2 hours. After cooling to room temperature, the reaction mixture was poured into aqueous saturate NaHCO3 solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica-gel (ethyl acetate/ hexane, 2/3-1/1) to give (Z)-2-imidazo[1,2-c]quinazolin-5-yl-1-(2-thienyl)ethenol (37.0 mg, 33% yield) as a yellow powder.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. additionthe reaction mixture was poured
  4. concentrationinto aqueous saturate NaHCO3 solution
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography on silica-gel (ethyl acetate/ hexane, 2/3-1/1)

Sources & evidence

ORD record
ord-cda7b906559441fe8e0dc5a4f0cffd29
Source dataset
uspto-grants-2012_03
Patent number
US08129386B2

Reaction notes

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