Hydrazine → 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazole-4-carbohydrazide

HRID 548106

Reaktionsgleichung

Reaktionsgleichung von HRID 548106
[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](OCC)=[O:14])[CH:10]=[N:9]2)=[C:5]([CH3:18])[O:4][N:3]=1.[NH2:19][NH2:20]>CCO>[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]([NH:19][NH2:20])=[O:14])[CH:10]=[N:9]2)=[C:5]([CH3:18])[O:4][N:3]=1

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 57944988Ethyl 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazole-4-carboxylate

Produkt 1

HCID 579449511-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazole-4-carbohydrazideAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazole-4-carboxylate (example 10-1c) (6 g, 24 mmol) and hydrazine (7.5 g, 240 mmol) were stirred in EtOH (100 mL) at reflux for 12 hours. The solution was concentrated on the rotovap and the solid product was triturated with ethyl acetate/hexanes (1/9) and dried under high vacuum to afford 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazole-4-carbohydrazide (5.5 g, 97%) as a pure white solid. 1H NMR (DMSO-d6, 400 MHz): δ2.11 (s, 3H), 2.39 (s, 3H), 5.15 (s, 2H), 7.81 (s, 1H), 8.17 (s, 1H), 9.31 (bs, 1H).

Aufarbeitung

  1. temperatureat reflux for 12 hours
  2. concentrationThe solution was concentrated on the rotovap
  3. customthe solid product was triturated with ethyl acetate/hexanes (1/9)
  4. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-17d5680100ba4a9a9adf5e772d955990
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939671B2

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