Sulfamic Acid → 1-phenyl-1H-pyrazole-4-carboxylic acid

HRID 1093767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1093767
S(=O)(=O)(O)N.[C:6]1([N:12]2[CH:16]=[C:15]([CH:17]=[O:18])[CH:14]=[N:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl([O-])=[O:20].[Na+]>O.CC(C)=O>[C:6]1([N:12]2[CH:16]=[C:15]([C:17]([OH:20])=[O:18])[CH:14]=[N:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

6

Edukt 3

HCID 5987Sulfamic AcidHCID 9520891-Phenyl-1H-pyrazole-4-carbaldehydeHCID 23668197Sodium Chlorite

Produkt 1

HCID 1210261-phenyl-1H-pyrazole-4-carboxylic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-Phenyl-1H-pyrazole (250 mg, 1.7 mmol) was added to a cold (0-4° C.) solution of DMF (1.5 g, 1.6 mL, 9.7 mmol) and POCl3 (1.86 g, 1.1 mL, 19.2 mmol) and stirring continued for 10 minutes. The resulting mixture was heated at 106° C. for 2.5 hrs. The reaction mixture was cooled and quenched with ice cold water, basified with 20% aqueous NaOH solution, the solid was collected to afford 330 mg (crude) of 1-phenyl-1H-pyrazole-4-carbaldehyde. 1H NMR (300 MHz, CDCl3): δ 10.0 (s, 1H), 8.45 (s, 1H), 8.2 (s, 1H), 7.75 (d, 2H), 7.55 (t, 2H), 7.45 (t, 1H). Sulphamic acid (253 mg, 2.6 mmol) in water (0.5 mL) was added at 0° C. to a mixture of phenyl-1H-pyrazole-4-carbaldehyde (0.5 g, 2.34 mmol) in acetone (3 mL). After 2 minutes sodium chlorite (315 mg, 3.5 mmol) was added and the resulting mixture was stirred at 0° C. for 30 minutes. Water was added and the solid obtained was isolated by filtration to afford 140 mg (85% yield) of 1-phenyl-1H-pyrazole-4-carboxylic acid.

Aufarbeitung

  1. customthe solid obtained
  2. customwas isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e804138af087416c99bbfa82f0de6682
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129376B2

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