Hydrochloric Acid → Bumetanide Impurity 118

HRID 596314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 596314
C(=O)([O-])[O-].[K+].[K+].[CH:7]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]([CH3:14])[CH:8]=1.Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([C:25]([OH:27])=[O:26])=[CH:18][C:17]=1[S:28]([NH2:31])(=[O:30])=[O:29].Cl>O>[N+:22]([C:21]1[CH:20]=[C:19]([CH:18]=[C:17]([S:28](=[O:30])(=[O:29])[NH2:31])[C:16]=1[O:13][C:12]1[CH:7]=[CH:8][C:9]([CH3:14])=[CH:10][CH:11]=1)[C:25]([OH:27])=[O:26])([O-:24])=[O:23]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 2879P-CresolHCID 11430Potassium CarbonateHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acid

Produkt 1

HCID 21312073Bumetanide Impurity 118

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

124 g (0.9 mol) of potassium carbonate are dissolved in 800 ml of water. To this solution, there are added portionwise 1.6 mols of p-cresol and subsequently 112 g (0.4 mol) of 2-chloro-3-nitro-5-carboxy-benzenesulphonamide and the solution is heated to 85° C. The whole is stirred for 16 hours at this temperature, cooled to 25°-30° C and acidified with concentrated hydrochloric acid to pH 1. The oil which thereupon separates is isolated from the aqueous phase and subjected to steam distillation. Alternatively, it is also possible to adjust to pH-value of 8-9, to extract the excess phenol with ethyl acetate and then to acidify the aqueous phase. After having separated in this manner the excess p-cresol, the product crystallises upon cooling. By recrystallisation from acetone/H2O, the 3-nitro-4-(4'-methylphenoxy)-5-sulphamoylbenzoic acid melting at 236° C is obtained.

Aufarbeitung

  1. temperaturecooled to 25°-30° C
  2. customThe oil which thereupon separates is isolated from the aqueous phase
  3. distillationsubjected to steam distillation
  4. extractionto extract the excess phenol with ethyl acetate
  5. customAfter having separated in this manner the excess p-cresol
  6. customthe product crystallises
  7. temperatureupon cooling
  8. customBy recrystallisation from acetone/H2O

Quellen und Nachweise

ORD-Eintrag
ord-3beca34a8fb449f3b09e6bc6a89ca24c
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04010273

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