Hydrochloric Acid → 1,4-Benzenedicarboxylic acid, 2,5-bis[(4-chlorophenyl)amino]-

HRID 2056968

Reaktionsgleichung

Reaktionsgleichung von HRID 2056968
[Cl: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]([Cl: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>[Cl: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]([Cl: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 147459351,4-Cyclohexadiene-1,4-dicarboxylic acid, 2,5-bis((4-chlorophenyl)amino)-, 1,4-dimethyl ester

Produkt 1

HCID 1705571,4-Benzenedicarboxylic acid, 2,5-bis[(4-chlorophenyl)amino]-Ausbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Dimethyl 2,5-bis{(4-chlorophenyl)amino}cyclohexa-1,4-diene-1,4-dicarboxylate (4.47 gm, 10 mmol), the sodium salt of 3-nitrobenzenesulphonic acid (2.3 gm; 10 mmol), ethanol (70 ml) and 1.0M sodium hydroxide (40 ml) 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 4.0 gm (96%) of 2,5-bis{(4-chlorophenyl)amino}terephthalic acid.

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-a8c76c812727443dbe2c9b61f7f883bb
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335771B2

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