Hydrochloric Acid → 2,5-Bis(4-fluoroanilino)benzene-1,4-dicarboxylic acid

HRID 2056971

Reaktionsgleichung

Reaktionsgleichung von HRID 2056971
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH2:14][C:13]([C:15]([O:17]C)=[O:16])=[C:12]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:11][C:10]=2[C:27]([O:29]C)=[O:28])=[CH:4][CH:3]=1.[Na].[N+](C1C=C(S(O)(=O)=O)C=CC=1)([O-])=O.[OH-].[Na+].Cl>O.C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[C:12]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[CH:11][C:10]=2[C:27]([OH:29])=[O:28])=[CH:6][CH:7]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 73873-Nitrobenzenesulfonic acidHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 21058671Dimethyl 2,5-bis{(4-fluorophenyl)amino}cyclohexa-1,4-diene-1,4-dicarboxylate

Produkt 1

HCID 227622072,5-Bis(4-fluoroanilino)benzene-1,4-dicarboxylic acidAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Dimethyl 2,5-bis{(4-fluorophenyl)amino}cyclohexa-1,4-diene-1,4-dicarboxylate (6.21 gm, 15 mmol), the sodium salt of 3-nitrobenzenesulphonic acid (3.6 gm; 16 mmol), ethanol (90 ml) and 1.0M sodium hydroxide (50 μl) were heated to reflux overnight under a nitrogen atmosphere. The bright yellow solution was allowed to cool and water (120 ml) was added. The mixture was acidified with conc. hydrochloric acid when a red solid precipitated out. This material was filtered off, washed with water and dried under vacuum over phosphorous pentoxide to give 5.6 gm (97%) of 2,5-bis{(4-fluorophenyl)amino}terephthalic acid λmax(ab) 295 nm, 380 nm. (0.1M sodium hydroxide)

Aufarbeitung

  1. temperatureto reflux overnight under a nitrogen atmosphere
  2. temperatureto cool
  3. customprecipitated out
  4. filtrationThis material was filtered off
  5. washwashed with water
  6. dry with materialdried under vacuum over phosphorous pentoxide

Quellen und Nachweise

ORD-Eintrag
ord-6f114d6c5a7e4824bd9e11625454975f
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335771B2

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