Propargyl bromide → 1,5-bis(4-methoxyphenyl)-3-(2-propynyloxy)-1H-1,2,4-triazole

HRID 584750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 584750
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[N:18][C:17]([OH:28])=[N:16]2)=[CH:11][CH:10]=1.Br[CH2:30][C:31]#[CH:32].C(OCC)(=O)C>CN(C)C=O.O>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[N:18][C:17]([O:28][CH2:32][C:31]#[CH:30])=[N:16]2)=[CH:13][CH:14]=1

Komponenten

7

Edukt 4

HCID 7842Propargyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1784890151,5-bis(4-methoxyphenyl)-1H-1,2,4-triazol-3-ol

Produkt 1

HCID 99675201,5-bis(4-methoxyphenyl)-3-(2-propynyloxy)-1H-1,2,4-triazoleAusbeute 43,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium carbonate (279 mg, 2.02 mmol) was added to a solution of 1,5-bis(4-methoxyphenyl)-1H-1,2,4-triazol-3-ol (200 mg, 0.673 mmol) in dimethylformamide (2 mL). After 5 minute stirring, 3-bromo-1-propyne (0.18 mL, 2.02 mmol) was added to the mixture and the mixture was stirred for 4 hours. Ethyl acetate and water were poured into the mixture. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (toluene-ethyl acetate 4:1). The desired product was washed with isopropyl ether, isolated by filtration, and dried in vacuo to give 1,5-bis(4-methoxyphenyl)-3-(2-propynyloxy)-1H-1,2,4-triazole (99 mg, 43.9% yield).

Aufarbeitung

  1. stirringthe mixture was stirred for 4 hours
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (toluene-ethyl acetate 4:1)
  7. washThe desired product was washed with isopropyl ether
  8. customisolated by filtration
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-90168e96d82441939c08161f81156b2e
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06927230B2

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