Hydrochloric Acid → 1-Phenyl-1H-1,2,3-triazole-4-carboxylic acid

HRID 1177928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177928
[Li+].[OH-].C([O:5][C:6]([C:8]1[N:9]=[N:10][N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)=[O:7])C.O.Cl>C1COCC1.O>[C:13]1([N:11]2[CH:12]=[C:8]([C:6]([OH:7])=[O:5])[N:9]=[N:10]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 5270623Ethyl 1-phenyl-1H-1,2,3-triazole-4-carboxylate

Produkt 1

HCID 5551941-Phenyl-1H-1,2,3-triazole-4-carboxylic acidAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

LiOH (80 mg, 1.9 mmol) was added to a stirred solution of 1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester (130 mg, 0.6 mmol) in THF:H2O (1:1, 4 mL), and the resulting mixture was stirred at room temperature for 45 min. The reaction mixture was concentrated under reduced pressure to get the residue. Cold water was then added and acidified it with 10% aqueous HCl, filtered the solid precipitated to afford 40 mg (35.4% yield) of 1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid. 1H NMR (DMSO-d6): δ 13.4 (bs, 1H), 9.4 (s, 1H), 8.0 (d, 2H), 7.7 (t, 2H), 7.6 (t, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto get the residue
  3. filtrationfiltered the solid
  4. customprecipitated

Quellen und Nachweise

ORD-Eintrag
ord-04592faf6f01405cae737a2eedb0c230
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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