Hydrochloric Acid → HCID 57587317, compound

HRID 2056966Notes

Reaction equation

HRID 2056966 reaction equation
[Br: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]([Br: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>[Br: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]([Br:26])=[CH:22][CH:21]=3)=[CH:11][C:10]=2[C:27]([OH:29])=[O:28])=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 73873-Nitrobenzenesulfonic acidHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 57587328Dimethyl-2,5-bis[(4-bromophenyl)amino]cyclohexa-1,4-diene-1,4-dicarboxylate

Product 1

HCID 57587317HCID 57587317, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Dimethyl 2,5-bis{(4-bromophenyl}amino]cyclohexa-1,4-diene-1,4-dicarboxylate (5.36 gm; 10 mmol) the sodium salt of 3-nitrobenzenesulphonic acid (2.3 gm; 10 mmol), ethanol (50 ml) and 1.0M sodium hydroxide (30 ml) were heated to reflux for 7 hours 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 magenta solid precipitated out. This material was filtered off, washed with water and dried under vacuum over phosphorous pentoxide to give 4.84 gm (96%) of 2,5-bis{(4-bromophenyl)amino}terephthalic acid.

Workup

  1. temperatureto reflux for 7 hours 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

Sources & evidence

ORD record
ord-20095c773c77449f855f867aa3eea920
Source dataset
uspto-grants-2008_02
Patent number
US07335771B2

Reaction notes

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