Hydrochloric Acid → 4-Fluorohippuric acid

HRID 4704

Reaktionsgleichung

Reaktionsgleichung von HRID 4704
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[F:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.Cl>[OH-].[Na+]>[F:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](=[O:12])[NH:1][CH2:2][C:3]([OH:5])=[O:4])=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 750GlycineHCID 678794-Fluorobenzoyl chloride

Produkt 1

HCID 6993414-Fluorohippuric acidAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel2×

Versuchsvorschrift

A solution of glycine (15 g, 0.2 mol) in 175 mL of 5% aqueous sodium hydroxide is cooled to 10° C. to 15° C. p-Fluorobenzoyl chloride (31.6 g, 0.2 mol) is then added dropwise to the mixture and stirred vigorously for 0.5 hour while maintaining the temperature of the mixture of about 10° C. to 15° C. The pH of the reaction mixture is maintained at pH>9 by the dropwise addition of 50% aqueous sodium hydroxide. The mixture is stirred at 10° C. to 15° C. for two hours and the resulting clear solution then acidified to pH-1 with concentrated HCl. The resulting product is filtered off, washed with water (2×100 mL) and air dried to give a white solid (30.8 g, 78.1%); mp=161°-163° C.

Aufarbeitung

  1. additionis then added dropwise to the mixture
  2. temperaturewhile maintaining
  3. additionthe temperature of the mixture of about 10° C. to 15° C
  4. stirringThe mixture is stirred at 10° C. to 15° C. for two hours
  5. filtrationThe resulting product is filtered off
  6. washwashed with water (2×100 mL) and air
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-cd9cee84bbb34d60b58548e31996ec0e
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727155

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