Urea → 3-Iodophthalic acid

HRID 21110

Reaktionsgleichung

Reaktionsgleichung von HRID 21110
N[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[C:11]([OH:13])=[O:12].[N+]([O-])([O-])=O.[Na+].[I-:19].[K+].NC(N)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>Cl>[I:19][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[C:11]([OH:13])=[O:12]

Komponenten

7

Edukt 5

HCID 1176UreaHCID 4875Potassium IodideHCID 24268Sodium NitrateHCID 24477Sodium ThiosulfateHCID 794903-Aminophthalic acid

Produkt 1

HCID 2382313-Iodophthalic acidAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

3-Aminophthalic acid (5.00 g, 27.6 mmol) was dissolved in 8.4 mol/L hydrochloric acid (60 mL), and the solution was added with an aqueous solution (10 mL) of sodium nitrate (2.0 g, 29 mmol) by drops under ice-cooling for 20 minutes, followed by stirring at the same temperature for 3 hours. Then, an aqueous solution (10 mL), in which potassium iodide (6.9 g, 41 mmol) and urea (291 mg) were dissolved, is added by drops to the mixture, followed by stirring at room temperature for 20 hours. The reaction mixture was added with 10% aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was washed with chloroform to obtain 3-iodophthalic acid (5.0 g, yield 62%).

Aufarbeitung

  1. temperaturecooling for 20 minutes
  2. additionis added by drops to the mixture
  3. stirringby stirring at room temperature for 20 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. washthe residue was washed with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-e0e207c6299d4555b2027fedb6fcecfc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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