2,5-Hexanedione → 3-Sulphamoyl-4-phenoxy-5-(2,5-dimethyl-1-pyrrolyl)-benzoic acid

HRID 47098

Reaction equation

HRID 47098 reaction equation
[S:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([NH2:21])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]([OH:10])=[O:9])(=[O:4])(=[O:3])[NH2:2].[CH2:22]([CH2:26][C:27](=O)[CH3:28])[C:23]([CH3:25])=O>C(O)(=O)C>[S:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N:21]2[C:27]([CH3:28])=[CH:26][CH:22]=[C:23]2[CH3:25])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]([OH:10])=[O:9])(=[O:3])(=[O:4])[NH2:2]

Participants

4

Reactant 2

HCID 80352,5-HexanedioneHCID 1199273-Amino-4-phenoxy-5-sulfamoylbenzoic acid

Product 1

HCID 128837293-Sulphamoyl-4-phenoxy-5-(2,5-dimethyl-1-pyrrolyl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-sulphamoyl-4-phenoxy-5-aminobenzoic acid (1.54 g=5 mmols; P. W. Feit, J. Med. Chem. 14, 432 (1971)), acetonylacetone (0.57 g=5 mmols) and 10 ml of glacial acetic acid is refluxed under N2 for 30 minutes, the red reaction solution is evaporated in vacuo and freed from residues of glacial acetic acid and water by adding benzene and evaporating azeotropically, the residue is dissolved in acetone, the solution is boiled with silica gel and filtered through a fine filter and the solution is concentrated to 50 ml and, after adding 50 ml of ethyl acetate, freed from acetone residues in vacuo, whereupon crystallisation takes place. After the purification procedure has been repeated, beige-coloured crystals with a melting point of 283°-286° (decomposition) result.

Workup

  1. temperatureis refluxed under N2 for 30 minutes
  2. customthe red reaction solution is evaporated in vacuo
  3. additionby adding benzene
  4. customevaporating azeotropically
  5. dissolutionthe residue is dissolved in acetone
  6. filtrationfiltered through
  7. filtrationa fine filter
  8. concentrationthe solution is concentrated to 50 ml
  9. additionafter adding 50 ml of ethyl acetate
  10. customfreed from acetone residues in vacuo, whereupon crystallisation
  11. customAfter the purification procedure
  12. custombeige-coloured crystals with a melting point of 283°-286° (decomposition) result

Sources & evidence

ORD record
ord-b4dd32f738804d1ab26ad29360b531ae
Source dataset
uspto-grants-1979_11
Patent number
US04176190

Linked notes

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