ethyl 2-bromo-3-oxo-3-phenylpropanoate → HCID 44384908, compound

HRID 2282167Notes

Reaction equation

HRID 2282167 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=[S:9])[NH2:8])=[CH:3][CH:2]=1.Br[CH:11]([C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[C:18]1([C:17]2[N:8]=[C:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[S:9][C:11]=2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 237819ethyl 2-bromo-3-oxo-3-phenylpropanoateHCID 27237884-Pyridinecarbothioamide

Product 1

HCID 44384908HCID 44384908, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of pyridine-4-carbothioamide (2.9 g, 21 mmol) in ethanol (150 mL) was added ethyl 2-bromo-3-oxo-3-phenylpropanoate (5.9 g, 22 mmol), and the mixture was heated under reflux for 8 hr. The reaction solution was allowed to cool to room temperature, and the solid was collected by filtration, washed with diethyl ether, dried, suspended in ethyl acetate (250 mL), and washed with saturated aqueous sodium bicarbonate solution (150 mL×2). The combined aqueous layer was extracted with ethyl acetate (100 mL×2). The combined organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was washed with diethyl ether, and collected by filtration to give the title compound (3.7 g, 57%) as a colorless solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hr
  3. filtrationthe solid was collected by filtration
  4. washwashed with diethyl ether
  5. customdried
  6. washwashed with saturated aqueous sodium bicarbonate solution (150 mL×2)
  7. extractionThe combined aqueous layer was extracted with ethyl acetate (100 mL×2)
  8. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  9. filtrationthe insoluble material was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. washThe residue was washed with diethyl ether
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c2c9754e53e44380a1315769e42d478b
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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