Acetic Acid → HCID 19886267, compound

HRID 654786Notes

Reaction equation

HRID 654786 reaction equation
S(=O)(=O)(O)O.C(O)(=O)C.C(OC([CH:15](C(OCC)=O)[C:16]([C:18]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)[N:20]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[N:19]=1)=[O:17])=O)C>O>[C:16]([C:18]1[CH:22]=[C:21]([C:23]2[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=2)[N:20]([C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)[N:19]=1)(=[O:17])[CH3:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 198861103-Bis(ethoxycarbonyl)acetyl-1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole

Product 1

HCID 19886267HCID 19886267, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of sulfuric acid (3.9 ml), acetic acid (23.6 ml) and water (19.6 ml) was added to 3-bis(ethoxycarbonyl)acetyl-1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole. The mixture was refluxed for 5 hours and concentrated. The residue was dissolved in ethyl acetate, and the solution was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (150 g) eluting with a mixture of chloroform and ethyl acetate (3:1) to give pale brown crystals of 3-acetyl-1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole (4.2 g).

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (150 g)
  8. washeluting with a mixture of chloroform and ethyl acetate (3:1)

Sources & evidence

ORD record
ord-8f28f142a2134e59a228f7c24b6431a0
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

Loading…