HCID 2778795, compound → HCID 178474418, compound

HRID 467863Notes

Reaction equation

HRID 467863 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>[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

4

Reactant 2

HCID 2778795HCID 2778795, compoundHCID 178475102HCID 178475102, compound

Product 1

HCID 178474418HCID 178474418, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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). The reaction mixture was stirred and refluxed for overnight. The solvent was evaporation under reduced pressure and diluted with water and extracted with ethyl acetate (75 ml×3) and organic layers were washed with brine, dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure and 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. temperaturerefluxed for overnight
  2. customevaporation under reduced pressure
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate (75 ml×3) and organic layers
  5. washwere washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue obtained
  10. customafter the evaporation of the solvent
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-99077d4200674b38a3e8873636f0402c
Source dataset
uspto-grants-2014_01
Patent number
US08623880B2

Reaction notes

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