Sulfuric Acid → HCID 12972727, compound

HRID 1860577Notes

Reaction equation

HRID 1860577 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:29])([F:28])[C:15](=O)[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26])=O.S(=O)(=O)(O)O>C(O)C(F)(F)F>[Cl:26][C:20]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1[C:17]1[N:1]([C:3]2[CH:8]=[CH:7][C:6]([S:9]([CH3:12])(=[O:10])=[O:11])=[CH:5][N:4]=2)[N:2]=[C:15]([C:14]([F:29])([F:13])[F:28])[CH:16]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 99642932-Hydrazino-5-(methanesulfonyl)-pyridineHCID 186241061-(2,4-Dichlorophenyl)-4,4,4-trifluorobutane-1,3-dione

Product 1

HCID 12972727HCID 12972727, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

To a mixture of the 2-hydrazino-5-(methylsulfonyl)pyridine (106 mg, 4.05 mmol) and 4,4,4-trifluoro-1-(2,4-dichlorophenyl)-1,3-butanedione (105 mg, 3.68 mmol) in dry trifluoroethanol (6 ml) was added a catalytic amount of concentrated sulfuric acid (about 0.25 ml) and the mixture was refluxed overnight. The reaction mixture was cooled to room temperature, concentrated, and diluted with water (25 ml) and neutralized with saturated NaHCO3 to pH about 7 and then extracted with EtOAc (50ml×3). The organic layer was washed with brine (100 ml), dried (MgSO4) and concentrated to give the crude solid. The solid was purified by flash chromatography eluting with ethyl acetate/hexane (1/4) to give the desired product as a white solid (134 mg, 83% yield).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. concentrationconcentrated
  3. additiondiluted with water (25 ml)
  4. extractionextracted with EtOAc (50ml×3)
  5. washThe organic layer was washed with brine (100 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give the crude solid
  9. customThe solid was purified by flash chromatography
  10. washeluting with ethyl acetate/hexane (1/4)

Sources & evidence

ORD record
ord-a2b2c34d9dd8456ca987d2ecbfb0aea3
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

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