HCID 2778795, compound → HCID 178474418, compound

HRID 1891093Notes

Reaction equation

HRID 1891093 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[C:7]([F:15])[CH:6]=1)=O.[C:16]([NH:19][C:20]([NH2:22])=[NH:21])(=[O:18])[CH3:17]>C(#N)C.C(OCC)(=O)C.O>[F:15][C:7]1[CH:6]=[C:5]([C:3]2[N:21]=[C:20]([NH:19][C:16](=[O:18])[CH3:17])[NH:22][CH:2]=2)[CH:10]=[CH:9][C:8]=1[C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 2

HCID 2778795HCID 2778795, compoundHCID 178475102HCID 178475102, compound

Product 1

HCID 178474418HCID 178474418, compoundYield 25.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-bromo-1-[3-fluoro-4-(trifluoromethyl)phenyl]ethanone (4.5 g, 15.73 mmol) in acetonitrile (45 ml) was added acetyl guanidine (2.38 g, 23.60 mmol) at room temperature. After refluxing for 4 h the reaction mixture was cooled to room temperature and diluted with ethyl acetate and water. The layers were separated. The aqueous layer was extracted 2-3 times with ethyl acetate and the combined organic layers were washed with water, followed by brine, dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure. The residue obtained after the evaporation of the solvent was purified by silica gel column chromatography using 2% methanol in chloroform to obtain 1.15 g of the product as a yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 2.07 (s, 3H), 7.58 (s, 1H), 7.69-7.78 (m, 3H), 11.31 (br s, 1H), 11.91 (br s, 1H).

Workup

  1. temperatureAfter refluxing for 4 h the reaction mixture
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted 2-3 times with ethyl acetate
  4. washthe combined organic layers were washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue obtained
  9. customafter the evaporation of the solvent
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-195548d086cc4e418ab2d5386cc316f3
Source dataset
uspto-grants-2013_08
Patent number
US08507503B2

Reaction notes

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