Hydrochloric Acid → 1-(1-ethoxyethyl)-4-(phenylethynyl)-1H-pyrazol-5-amine

HRID 2205761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2205761
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[N:11][NH:12][C:13]=2[NH:14]C(=O)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:18]([O:20][CH:21]=[CH2:22])[CH3:19].Cl>C(Cl)Cl.O1CCOCC1>[CH2:18]([O:20][CH:21]([N:12]1[C:13]([NH2:14])=[C:9]([C:8]#[C:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:10]=[N:11]1)[CH3:22])[CH3:19]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 8023Ethyl vinyl etherHCID 86717261N-(4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide

Produkt 1

HCID 867172621-(1-ethoxyethyl)-4-(phenylethynyl)-1H-pyrazol-5-amineAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 312751,4-DioxaneKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A solution of N-(4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide (17.6 g, 78 mmol), ethoxyethene (11.2 mL, 117 mmol) and HCl in 1,4-dioxane (1 mL, 4 mmol) in CH2Cl2 (520 mL) was stirred at room temperature for 1 h and concentrated in vacuo. The residue was dissolved in ethanol (260 mL) and 25% aq. NaOH solution (260 mL) and the reaction mixture was heated to 75° C. for 4 h and cooled to room temperature. The ethanol was part concentrated in vacuo and the resulting solid collected by filtration, washed with water and minimum cold ethanol and dried in vacuo to provide the title compound as a solid (16 g).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethanol (260 mL)
  3. temperaturecooled to room temperature
  4. concentrationconcentrated in vacuo
  5. filtrationthe resulting solid collected by filtration
  6. washwashed with water and minimum cold ethanol
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-90f2374cac1140f699aa2d14b21fb4a5
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09371332B2

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