Phenol → 3-(Aminosulfonyl)-5-nitro-4-phenoxybenzoic acid

HRID 918599

Reaktionsgleichung

Reaktionsgleichung von HRID 918599
Cl[C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[C:18]1([OH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>O>[N+:15]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])[C:2]=1[O:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:6]([OH:8])=[O:7])([O-:17])=[O:16]

Komponenten

5

Edukt 3

HCID 996PhenolHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acidHCID 516892Sodium Bicarbonate

Produkt 1

HCID 1199263-(Aminosulfonyl)-5-nitro-4-phenoxybenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 4-chloro-3-nitro-5-sulphamyl-benzoic acid (140 g), phenol (100 g), sodium bicarbonate (170 g), and water (1000 ml) was heated to 85°C while stirring and kept at this temperature for 16 hours. After cooling to 4°C, the precipitated sodium salt of 3-nitro-4-phenoxy-5-sulphamyl-benzoic acid was filtered off and washed with ice-water. The sodium salt was dissolved in boiling water (3000 ml), and the 3-nitro-4-phenoxy-5-sulphamyl-benzoic acid was precipitated by the addition of 4N hydrochloric acid. After cooling, the acid was isolated by suction and dried. The melting point was 255°-256°C.

Aufarbeitung

  1. temperatureAfter cooling to 4°C
  2. filtrationthe precipitated sodium salt of 3-nitro-4-phenoxy-5-sulphamyl-benzoic acid was filtered off
  3. washwashed with ice-water
  4. dissolutionThe sodium salt was dissolved
  5. customthe 3-nitro-4-phenoxy-5-sulphamyl-benzoic acid was precipitated by the addition of 4N hydrochloric acid
  6. temperatureAfter cooling
  7. customthe acid was isolated by suction
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e6e12beb5c85441aa3ad9d9832ad79b7
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03971819

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