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Hydrochloric Acid → 5-Amino-3-mercapto-4-phenoxybenzoic acid

HRID 1605512
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1605512
[Na].[N+:2]([C:5]1[C:6]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:7]([S:14](O)=O)[CH:8]=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])([O-])=O.Cl>C(O)C.[Zn]>[NH2:2][C:5]1[C:6]([O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:7]([SH:14])[CH:8]=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 215201035-Nitro-4-phenoxy-3-sulfinobenzoic acid

Produkt 1

HCID 215201075-Amino-3-mercapto-4-phenoxybenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 702Ethanol
Lösungsmittel

Versuchsvorschrift

Zinc powder (38 g) is added to a warm solution (70° C) of the mono sodium salt of 5-nitro-4-phenoxy-3-sulfinobenzoic acid (10 g) in ethanol (190 ml), and while stirring 5 N hydrochloric acid (190 ml) is added dropwise. The reaction mixture is kept under nitrogen for an additional 2 hours at 70° C. After cooling and filtration, the ethanol is distilled off in vacuo. After standing in a refrigerator for 16 hours, the precipitated material is collected by filtration and washed with concentrated hydrochloric acid (15 ml). This material is then suspended in water (300 ml) and the pH adjusted to 2 by addition of 2 N sodium hydroxide. The obtained crude 5-amino-3-mercapto-4-phenoxybenzoic acid is collected and recrystallized from aqueous ethanol. The acid is obtained with a melting point of 199°-200° C.

Aufarbeitung

  1. additionis added dropwise
  2. temperatureAfter cooling
  3. filtrationfiltration
  4. distillationthe ethanol is distilled off in vacuo
  5. waitAfter standing in a refrigerator for 16 hours
  6. filtrationthe precipitated material is collected by filtration
  7. washwashed with concentrated hydrochloric acid (15 ml)
  8. additionthe pH adjusted to 2 by addition of 2 N sodium hydroxide

Quellen und Nachweise

ORD-Eintrag
ord-56a4b015893047a89ea4abb5f019fa9d
Quelldatensatz
uspto-grants-1976_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03950376

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