Water → HCID 89586219, compound

HRID 1747758Notes

Reaction equation

HRID 1747758 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7](=[O:24])[C:8](=[N:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[C:9](=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:9]([C:8]1[C:7](=[O:24])[C:3]2[O:4][CH:5]=[CH:6][C:2]=2[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N:12]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 178468330HCID 178468330, compound

Product 1

HCID 89586219HCID 89586219, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 1-(3-bromofuran-2-yl)-2-{[3-(trifluoromethyl)phenyl]hydrazono}butane-1,3-dione (1.59 g) and potassium carbonate (0.817 g) in DMF (10 mL) was stirred at 90° C. for 4 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) and recrystallized from hexane/ethyl acetate to give the title compound (683 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  6. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-c3369e1635ce4e7d9b5fc298e12012b9
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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