Hydrochloric Acid → Benzoic acid,3-amino-5-(aminosulfonyl)-4-(3-chlorophenoxy)-

HRID 918609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 918609
[Cl-].[NH4+].Cl.[Cl:4][C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][CH:27]=1)[O:8][C:9]1[C:17]([S:18](=[O:21])(=[O:20])[NH2:19])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[N+:22]([O-])=O.[OH-].[Na+]>[Fe].O>[NH2:22][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([S:18](=[O:20])(=[O:21])[NH2:19])[C:9]=1[O:8][C:7]1[CH:25]=[CH:26][CH:27]=[C:5]([Cl:4])[CH:6]=1)[C:13]([OH:15])=[O:14]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 215060844-(m-Chlorophenoxy)-3-nitro-5-sulphamyl-benzoic acid

Produkt 1

HCID 21506064Benzoic acid,3-amino-5-(aminosulfonyl)-4-(3-chlorophenoxy)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of ammonium chloride (1.2 g), metallic iron powder (11 g), concentrated hydrochloric acid (0.05 ml), and water (30 ml) was heated on a steam bath. 4-(m-Chlorophenoxy)-3-nitro-5-sulphamyl-benzoic acid (3 g) was added while stirring, and the heating was continued for 6 hours. Then 1N sodium hydroxide (50 ml) was added, and the reaction mixture was filtered. The filter cake was washed twice with 1N sodium hydroxide (50 ml each time). The combined filtrates were adjusted to a pH of 2.5 by the addition of 4N hydrochloric acid. After cooling, the precipitated 3-amino-4-(m-chlorophenoxy)-5-sulphamyl-benzoic acid was collected by suction, and recrystallized from aqueous ethanol. The melting point was 239°-240°C.

Aufarbeitung

  1. temperaturewas heated on a steam bath
  2. filtrationthe reaction mixture was filtered
  3. washThe filter cake was washed twice with 1N sodium hydroxide (50 ml each time)
  4. additionThe combined filtrates were adjusted to a pH of 2.5 by the addition of 4N hydrochloric acid
  5. temperatureAfter cooling
  6. customthe precipitated 3-amino-4-(m-chlorophenoxy)-5-sulphamyl-benzoic acid was collected by suction
  7. customrecrystallized from aqueous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-c78fdadb0c204efebd9aa6699766b8c3
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03971819

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