Hydrochloric Acid → 3-[(Ethyloxy)methyl]-1-(1-methylethyl)-1H-pyrazol-5-amine

HRID 1472567

Reaktionsgleichung

Reaktionsgleichung von HRID 1472567
[CH2:1]([O:3][CH2:4][C:5](=O)[CH2:6][C:7]#[N:8])[CH3:2].Cl.[CH:11]([NH:14][NH2:15])([CH3:13])[CH3:12].Cl>C(O)C>[CH2:1]([O:3][CH2:4][C:5]1[CH:6]=[C:7]([NH2:8])[N:14]([CH:11]([CH3:13])[CH3:12])[N:15]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 855731-Isopropylhydrazine hydrochlorideHCID 575169104-Ethoxy-3-oxobutanenitrile

Produkt 1

HCID 575169093-[(Ethyloxy)methyl]-1-(1-methylethyl)-1H-pyrazol-5-amineAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a 25 mL round bottom was added 4-(ethyloxy)-3-oxobutanenitrile (550 mg, 4.33 mmol), isopropyl hydrazine hydrochloride (478 mg, 4.33 mmol), and HCl (2.163 mL, 4.33 mmol) in Ethanol (10 mL). The reaction mixture was stirred at the room temperature overnight. The reaction mixture was then evaporated, and partitioned between 20 mL of ethyl acetate and 20 mL of 1 M Na2CO3. The organic layer was washed with brine, filtered and evaporated. 3-[(Ethyloxy)methyl]-1-(1-methylethyl)-1H-pyrazol-5-amine (520 mg, 2.84 mmol, 65.6% yield) was isolated as yellow oil. The product was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) ppm 1.09 (t, J=7.07 Hz, 3 H) 1.26 (d, J=6.57 Hz, 6 H) 3.40 (q, J=6.91 Hz, 2 H) 4.16 (s, 2 H) 4.32 (quin, J=6.57 Hz, 1 H) 5.06 (s, 2 H) 5.22 (s, 1 H)

Aufarbeitung

  1. customThe reaction mixture was then evaporated
  2. custompartitioned between 20 mL of ethyl acetate and 20 mL of 1 M Na2CO3
  3. washThe organic layer was washed with brine
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9c31f07cab6c4230930095f11d757b62
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012479B2

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