StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Propargyl bromide → 2-(1,1-Dimethylethyl)-2,4-dihydro-5-phenyl-4-(2-propyn-1-yl)-3H-1,2,4-triazol-3-one

HRID 892699
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 892699
[C:1]([N:5]1[C:9](=[O:10])[N:8]=[C:7]([C:11]2[CH:16]=[CH:15][CH2:14][CH2:13][CH:12]=2)[NH:6]1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+].[CH2:29](Br)[C:30]#[CH:31]>C1(C)C=CC=CC=1.O>[C:1]([N:5]1[C:9](=[O:10])[N:8]([CH2:31][C:30]#[CH:29])[C:7]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[N:6]1)([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7842Propargyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178448764HCID 178448764, Verbindung

Produkt 1

HCID 190109342-(1,1-Dimethylethyl)-2,4-dihydro-5-phenyl-4-(2-propyn-1-yl)-3H-1,2,4-triazol-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of crude 345 g (1.2 mol) of 1-t-butyl-4-H-3-phenyl-1,2,4-triazol-5-one and 3.5 L of ethyl acetate containing 0.03% water was stirred at room temperature and 190 g (1.67 mol) of solid potassium carbonate (K2CO3) was added. The mixture was heated at reflux for 0.5 h and 248 g (1.67 mol) of an 80% weight solution of propargyl bromide in toluene was added dropwise over 30 minutes. Refluxing was continued for an additional 3 h. The mixture was allowed to cool to room temperature, diluted with 2 L of water and stirred for 15 min. The organic layer was separated, washed with brine and dried over magnesium sulfate (MgSO4). Removal of the solvent left 300 g of an oil which was crystallized from 500 mL of ether and 1500 mL of hexanes to furnish 180 g of the desired compound, mp 82°-83° C.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 0.5 h
  3. temperatureRefluxing
  4. temperatureto cool to room temperature
  5. stirringstirred for 15 min
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate (MgSO4)
  9. customRemoval of the solvent
  10. waitleft 300 g of an oil which
  11. customwas crystallized from 500 mL of ether and 1500 mL of hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4b75f26b13bf4444b823f3624750d2d0
Quelldatensatz
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05120347

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion