4-Pentynoic acid → 5-(But-3-ynyl)-3-o-tolyl-1,2,4-oxadiazole

HRID 1189070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1189070
[OH:1][N:2]=[C:3]([NH2:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10].[C:12](O)(=O)[CH2:13][CH2:14][C:15]#[CH:16].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>O1CCOCC1>[CH2:15]([C:16]1[O:1][N:2]=[C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[CH3:10])[N:11]=1)[CH2:14][C:13]#[CH:12]

Komponenten

6

Edukt 4

HCID 224644-Pentynoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3098087N-Hydroxy-2-methyl-benzamidine

Produkt 1

HCID 860869225-(But-3-ynyl)-3-o-tolyl-1,2,4-oxadiazoleAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a reactor tube, a mixture of N′-hydroxy-2-methylbenzamidine (555 mg, 3.7 mmol), 4-pentynoic acid (363 mg, 3.7 mmol), HOBT (0.56 g, 3.7 mmol) and EDCI.HCl (1.06 g, 5.55 mmol) in dioxane (7.4 mL) was stirred at R.T for 3h. After this time the mixture was heated at 80° C. overnight in a reaction block. The mixture was concentrated. The organic layer was washed with water, NaOH 1N and water. The solvent was evaporated in a Genevac for 75 min at 40° C. using the low boiling point program. The crude product was purified by flash chromatography (Prepacked 10 g silicagel column) with DCM as eluent to afford 250 mg of 5-(but-3-ynyl)-3-o-tolyl-1,2,4-oxadiazole (Yield: 32%) as yellow oil.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. washThe organic layer was washed with water, NaOH 1N and water
  3. customThe solvent was evaporated in a Genevac for 75 min at 40° C.
  4. customThe crude product was purified by flash chromatography (Prepacked 10 g silicagel column) with DCM as eluent

Quellen und Nachweise

ORD-Eintrag
ord-3d267b04c5ef42609df73af5d66d9f85
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674106B2

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