Hydrogen iodide → HCID 19886245, compound

HRID 654790Notes

Reaction equation

HRID 654790 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=3)=[CH:12][C:11]([C:24]([O:26]CC)=[O:25])=[N:10]2)=[CH:5][CH:4]=1.I>C(O)(=O)C>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=3)=[CH:12][C:11]([C:24]([OH:26])=[O:25])=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 10763513HCID 10763513, compound

Product 1

HCID 19886245HCID 19886245, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 1-(4-methoxyphenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole-3-carboxylate (2 g) and hydriodic acid (57%, 5 ml) in acetic acid (10 ml) was refluxed for 5 hours. The reaction mixture was concentrated and the residue was triturated in an aqueous solution of sodium bisulfite giving a powder. This crude powder was purified by column chromatography on silica gel (80 g) eluting with a mixture of chloroform and methanol to give a powder of 1-(4-hydroxyphenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole-3-carboxylic acid (0.86 g).

Workup

  1. temperaturewas refluxed for 5 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was triturated in an aqueous solution of sodium bisulfite giving a powder
  4. customThis crude powder was purified by column chromatography on silica gel (80 g)
  5. washeluting with a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-f9f18801de2a412b9bbe3fe2f8b2e665
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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