Sulfuric Acid → HCID 4017524, compound

HRID 2180867Notes

Reaction equation

HRID 2180867 reaction equation
Cl.[F:2][C:3]([F:14])([F:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11]N)=[CH:7][CH:6]=1.[C:15]([OH:22])(=[O:21])[CH2:16][CH2:17][C:18]([CH3:20])=O.S(=O)(=O)(O)O>O>[CH3:20][C:18]1[NH:11][C:8]2[C:9]([C:17]=1[CH2:16][C:15]([OH:22])=[O:21])=[CH:10][C:5]([O:4][C:3]([F:14])([F:13])[F:2])=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 11579Levulinic AcidHCID 27773284-(Trifluoromethoxy)phenylhydrazine hydrochloride

Product 1

HCID 4017524HCID 4017524, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-trifluoromethoxyphenylhydrazine hydrochloride (1 g), levulinic acid (1.3 g) and 10% aqueous sulfuric acid (20 ml) was stirred for 6 hours under a nitrogen atmosphere at 80° C. The reaction mixture was allowed to cool, water was added, and then extraction was performed with ethyl acetate and the organic layer was concentrated under reduced pressure. Saturated sodium bicarbonate water was added to the obtained residue and vigorously stirred therewith, and then dichloromethane was added and the mixture was again vigorously stirred. The aqueous layer was collected, rendered acidic with concentrated aqueous hydrochloric acid, and then extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, to obtain 0.40 g of the title compound as a colorless powder (31% yield).

Workup

  1. temperatureto cool
  2. extractionextraction
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. additionSaturated sodium bicarbonate water was added to the obtained residue
  5. stirringvigorously stirred
  6. additiondichloromethane was added
  7. stirringthe mixture was again vigorously stirred
  8. customThe aqueous layer was collected
  9. extractionextracted with ethyl acetate
  10. dry with materialThe organic layer was dried over sodium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab8bc3db7b5442f7897731ac01fdaff9
Source dataset
uspto-grants-2005_05
Patent number
US06887890B2

Reaction notes

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