Sulfuric Acid → HCID 178508292, compound

HRID 467864Notes

Reaction equation

HRID 467864 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[N:13]=[C:14]([NH:17]C(=O)C)[NH:15][CH:16]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].OS(O)(=O)=O.[K]>CO.O>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[N:13]=[C:14]([NH2:17])[NH:15][CH:16]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 5462222PotassiumHCID 178474418HCID 178474418, compound

Product 1

HCID 178508292HCID 178508292, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of Step 1 intermediate (1.1 g, 3.829 mmol) in a mixture of methanol (20 ml) and water (20 ml) was added conc. H2SO4 (2 ml) and the resulting mixture was refluxed for 24 h. The reaction mixture was cooled to room temperature, saturated solution of potassium carnonate was added and extracted with ethyl acetate (2×50 ml). The organic layers were combined and dried over 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 5% methanol in chloroform to obtain 290 mg of the product as a yellow solid; 1H NMR (300 MHz, DMSO-d6): δ 5.55 (br s, 2H), 7.32 (s, 1H), 7.59-7.67 (m, 3H), 11.30 (br s, 1H).

Workup

  1. temperaturethe resulting mixture was refluxed for 24 h
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue obtained
  7. customafter the evaporation of the solvent
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ca7acc80829b430a888f4a37c71564c4
Source dataset
uspto-grants-2014_01
Patent number
US08623880B2

Reaction notes

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