Sulfuric Acid → HCID 13758016, compound

HRID 1506858Notes

Reaction equation

HRID 1506858 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[C:16](C)([C:22](OCC)=O)[C:17]([O:19]CC)=[O:18]>C(O)(=O)C.O>[F:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[CH:16]([CH3:22])[C:17]([OH:19])=[O:18]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 13758014HCID 13758014, compound

Product 1

HCID 13758016HCID 13758016, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Concentrated sulfuric acid (7.5 mL) was added to compound (4) obtained above (7.09 g, 22.6 mmol) in acetic acid (26 mL) and water (18 mL), and the obtained mixture was heated to reflux for 12 hours. After completion of the reaction, the mixture was cooled and concentrated under reduced pressure, and the residue was extracted with dichloromethane. The extract was washed with saturated saline and water and dried (over sodium sulfate). The solvent was then distilled off under reduced pressure to give 3.72 g (77%) of compound (5) of interest as clear reddish brown oil.

Workup

  1. temperatureto reflux for 12 hours
  2. customAfter completion of the reaction
  3. temperaturethe mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. extractionthe residue was extracted with dichloromethane
  6. washThe extract was washed with saturated saline and water
  7. dry with materialdried (over sodium sulfate)
  8. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-5094f36c55a34219922f96706fd6757b
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

Loading…