[(4-Iodophenyl)sulfonyl]-2-pyridylamine → 2-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoic acid

HRID 743001Notes

Reaction equation

HRID 743001 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:15])=[C:7]([CH:14]=1)[C:8]([O:10]C(C)C)=[O:9])=[CH2:2].I[C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1>>[OH:15][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[CH:2][C:17]2[CH:18]=[CH:19][C:20]([S:23]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)(=[O:25])=[O:24])=[CH:21][CH:22]=2)=[CH:14][C:7]=1[C:8]([OH:10])=[O:9]

Participants

3

Reactant 2

HCID 1143526[(4-Iodophenyl)sulfonyl]-2-pyridylamineHCID 19423367Isopropyl 5-ethenyl-2-hydroxybenzoate

Product 1

HCID 543430162-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoic acidYield 40%

Procedure

Isopropyl 5-ethenyl-2-hydroxybenzoate was reacted with 4-iodo-N-(2-pyridinyl)benzenesulfonamide similarly to the procedure of Example 5c. After the reaction, the solvent was evaporated, toluene was added and the suspension filtered and washed with toluene. After drying on the filter and washing with water the material was hydrolyzed and precipitated similarly to the procedure of Example 3c. Yield 40%

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated
  3. additiontoluene was added
  4. filtrationthe suspension filtered
  5. washwashed with toluene
  6. customAfter drying on the
  7. filtrationfilter
  8. washwashing with water the material
  9. customprecipitated similarly to the procedure of Example 3c

Sources & evidence

ORD record
ord-76e411d9c52446e183b5f60c4666df1f
Source dataset
uspto-grants-1996_09
Patent number
US05556855

Reaction notes

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