Реакция #75376

Уравнение реакции

3-sulphamoyl-4-phenoxy-5-aminobenzoic acid

acetonylacetone

→

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

Растворители

acetic acid

Условия реакции

Обработка

1. 1
   Температураis refluxed under N2 for 30 minutes
2. 2
   Другоеthe red reaction solution is evaporated in vacuo
3. 3
   workup.ADDITIONby adding benzene
4. 4
   Другоеevaporating azeotropically
5. 5
   workup.DISSOLUTIONthe residue is dissolved in acetone
6. 6
   Фильтрацияfiltered through
7. 7
   Фильтрацияa fine filter
8. 8
   Концентрированиеthe solution is concentrated to 50 ml
9. 9
   workup.ADDITIONafter adding 50 ml of ethyl acetate
10. 10
    Другоеfreed from acetone residues in vacuo, whereupon crystallisation
11. 11
    ДругоеAfter the purification procedure
12. 12
    Другоеbeige-coloured crystals with a melting point of 283°-286° (decomposition) result

Методика

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.

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