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

HRID 1686284

Reaktionsgleichung

Reaktionsgleichung von HRID 1686284
[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-6d2fe02a27db4293a79b994ddfd291dc
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148544B2

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