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Methyl iodide → 1-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-difluoromethyl-4,5-dihydro-4-methyl-1,2,4-triazol-5(1H)-one

HRID 1382155
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1382155
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[NH:16][C:15]([CH:19]([F:21])[F:20])=[N:14]1.[C:22](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[N:16]([CH3:22])[C:15]([CH:19]([F:20])[F:21])=[N:14]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1357451031-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-difluoromethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one

Produkt 1

HCID 143924861-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-difluoromethyl-4,5-dihydro-4-methyl-1,2,4-triazol-5(1H)-oneAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180
Acetone
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A stirred mixture of 4.0 g (0.012 mole) of 1-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-difluoromethyl-4,5-dihydro-1,2,4-triazol-5(1H)-one and 4.1 g (0.03 mole) of potassium carbonate in 160 mL of acetone was heated at reflux for 0.5 hours then cooled to about 50° C. Methyl iodide, 8.4 g (0.06 mole), was added and the mixture stirred at 45° for one hour then at reflux for one hour. The mixture was cooled to room temperature and evaporated under reduced pressure to leave an oil. This oil was partitioned between methylene chloride and water. The organic phase was washed with a 10% aqueous sodium hydroxide solution and then dried over anhydrous magnesium sulfate. The mixture was filtered and the filtrate evaporated under reduced pressure to leave an oil. This oil solidified when stirred with petroleum ether and upon filtration provided 2.6 g of 1-[2,4-dichloro-5-(1-methylethoxy)phenyl]-3-difluoromethyl-4,5-dihydro-4-methyl-1,2,4 -triazol-5-(1H)-one (mp 95°-97° C).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 0.5 hours
  3. temperatureat reflux for one hour
  4. temperatureThe mixture was cooled to room temperature
  5. customevaporated under reduced pressure
  6. customto leave an oil
  7. customThis oil was partitioned between methylene chloride and water
  8. washThe organic phase was washed with a 10% aqueous sodium hydroxide solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe mixture was filtered
  11. customthe filtrate evaporated under reduced pressure
  12. customto leave an oil

Quellen und Nachweise

ORD-Eintrag
ord-100b7c3c3cc648009f70b9f2f08aec05
Quelldatensatz
uspto-grants-1989_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04806145

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