Sulfuric Acid → HCID 9947370, compound

HRID 1860590Notes

Reaction equation

HRID 1860590 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:5][N:4]=1)[NH2:2].[F:13][C:14]([F:27])([F:26])[C:15](=O)[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O.S(=O)(=O)(O)O>C(O)C(F)(F)F.O.C([O-])(O)=O.[Na+]>[CH3:12][S:9]([C:6]1[CH:7]=[CH:8][C:3]([N:1]2[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:16][C:15]([C:14]([F:13])([F:26])[F:27])=[N:2]2)=[N:4][CH:5]=1)(=[O:10])=[O:11]

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 675894,4,4-Trifluoro-1-phenyl-1,3-butanedioneHCID 99642932-Hydrazino-5-(methanesulfonyl)-pyridine

Product 1

HCID 9947370HCID 9947370, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 64092,2,2-TrifluoroethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of the 2-hydrazino-5-(methylsulfonyl)pyridine (456 mg, 2.04 mmol) and 4,4,4-trifluoro-1-phenyl-1,3-butanedione (441 mg, 2.04 mmol) in dry trifluoroethanol (30 ml) was added a catalytic amount of concentrated sulfuric acid (-0.5 ml) and the mixture was refluxed overnight. The reaction mixture was cooled to room temperature and diluted with water 50 ml and neutralized with saturated NaHCO3 to PH˜7 and then extracted with EtOAc (50 ml×3). The organic layer was washed with brine (25 ml), dried (MgSO4) and concentrated to give the crude solid. The crude solid was recrystallized in ethanol to provide a desired product as a crystalline white solid (337 mg, 45% yield).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. extractionextracted with EtOAc (50 ml×3)
  3. washThe organic layer was washed with brine (25 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give the crude solid
  7. customThe crude solid was recrystallized in ethanol

Sources & evidence

ORD record
ord-bc688cd829b54794b945a6a8c6d02bc8
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

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