Glycine → Phenylglycin-o-carbonsaure

HRID 582652Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582652
[OH-].[K+].[C:3]([O-])([O-:5])=[O:4].[K+].[K+].Br[C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1C(O)=O.[NH2:19][CH2:20][C:21]([OH:23])=[O:22]>O>[C:10]1([N:19]([C:3]([OH:5])=[O:4])[CH2:20][C:21]([OH:23])=[O:22])[CH:11]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 750GlycineHCID 69402-Bromobenzoic acidHCID 11430Potassium CarbonateHCID 14797Potassium Hydroxide

Produkt 1

HCID 53420527Phenylglycin-o-carbonsaureAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of KOH (25 g, 440 mmol) and K2CO3 (25 g, 180 mmol) in H2O (400 mL) was added 2-bromobenzoic acid, (38.2 g, 190 mmol), followed by glycine (25 g, 330 mmol) and CuBr (540 mg, 3.76 mmol). This mixture was heated at reflux for 4 h. After cooling to room temperature, the mixture was filtered over a fritted funnel to remove traces of Cu and the filtrate was acidified to pH 3 with concentrated HCl. The precipitate was collected and dried to obtain 32.44 g (88%) of the title compound, mp 225.9-226.2° C. (decomp., white foam); 1H NMR (DMSO-d6) δ 12.4 (br, 1H), 8.06 (br, 1H), 7.80 (m, 1H), 7.35 (m, 1H), 6.60 (m, 2H), 3.99 (s, 2H); 13C NMR (DMSO-d6) δ 171.8, 169.7, 150.0, 134.4, 131.7, 114.7, 111.5, 110.6, 44.4; MS (EI, m/z) 195 (M+).

Aufarbeitung

  1. temperatureThis mixture was heated
  2. temperatureat reflux for 4 h
  3. filtrationthe mixture was filtered over a fritted funnel
  4. customto remove traces of Cu
  5. customThe precipitate was collected
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-54fcd9d72d344f49a204799c8a08a54f
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925647

Notizen zur Reaktion

Wird geladen…