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

HRID 47099

Reaktionsgleichung

Reaktionsgleichung von HRID 47099
[S:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([CH2:21][CH2:22][NH2:23])[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].[CH2:24]([CH2:28][C:29](=O)[CH3:30])[C:25]([CH3:27])=O.[Al]>CN(C)P(=O)(N(C)C)N(C)C>[S:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([CH2:21][CH2:22][N:23]2[C:29]([CH3:30])=[CH:28][CH:24]=[C:25]2[CH3:27])[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]

Komponenten

5

Edukt 3

HCID 80352,5-HexanedioneHCID 5359268AluminumHCID 127957173-Sulphamoyl-4-phenoxy-5-[beta-aminoethyl]-benzoic acid

Produkt 1

HCID 130210843-Sulphamoyl-4-phenoxy-5-[beta-(2,5-dimethyl-1-pyrrolyl)-ethyl]-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12679HexamethylphosphoramideLösungsmittel

Versuchsvorschrift

A mixture of 3-sulphamoyl-4-phenoxy-5-[β-aminoethyl]-benzoic acid (5.0 g=1.35 mmols; see Example 3 for the preparation), acetonylacetone (1.85 g, approximately 16.2 mmols) and hexamethylphosphoric acid triamide (Hexametapol; 25 ml) is warmed at 100° for 30 minutes under N2 in an apparatus which has been protected against incident light by covering it with aluminium foil, and the reaction solution is worked up as follows, with strict exclusion of light throughout: pouring into ice-water (50 ml) and extracting with ethyl acetate, washing the extract with water, drying and filtering and evaporating the filtrate. The crude product is recrystallised from chloroform/cyclohexane with the addition of active charcoal and gives pale orange-coloured, light-sensitive crystals, melting point>210° (decomposition).

Aufarbeitung

  1. temperatureis warmed at 100° for 30 minutes under N2 in an apparatus which
  2. extractionextracting with ethyl acetate
  3. washwashing the
  4. extractionextract with water
  5. customdrying
  6. filtrationfiltering
  7. customevaporating the filtrate
  8. customThe crude product is recrystallised from chloroform/cyclohexane with the addition of active charcoal
  9. customgives pale orange-coloured

Quellen und Nachweise

ORD-Eintrag
ord-970005fb4a7e42419affa6245d0b5231
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04176190

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