Water → HCID 69118047, Verbindung

HRID 889825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889825
C(O)(=O)C(O)=O.[CH2:7]([NH:11][NH2:12])[CH2:8][CH2:9][CH3:10].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=O)[CH2:21][N:22]2C(=O)CS[C:23]2=[O:28])=[CH:16][CH:15]=1.C(N(CC)CC)C.O>CO>[CH2:7]([N:11]1[C:23](=[O:28])[NH:22][CH2:21][C:20]([C:17]2[CH:16]=[CH:15][C:14]([Cl:13])=[CH:19][CH:18]=2)=[N:12]1)[CH2:8][CH2:9][CH3:10]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 162021Butylhydrazine oxalateHCID 12061653-[2-(4-Chlorophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione

Produkt 1

HCID 69118047HCID 69118047, VerbindungAusbeute 22,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Butylhydrazine oxalate (41 g, 230 mmol) and 40 g of 3-(2-(4-chlorophenyl)-2-oxo-ethyl)-thiazolidine-2,4-dione (161 mmol) in 2200 mL of methanol were cooled in an ice bath and treated with 30.3 g (300 mmol) of triethylamine. The reaction mixture was stirred at room temperature for 30 minutes, then refluxed overnight. The reaction mixture was cooled and 400 mL of water was added. This mixture was extracted with ethyl acetate. The organic phase was washed twice with 10% aqueous sodium hydroxide solution, then dried and stripped. The solids obtained were recrystallized from ethyl acetate/hexane to give 9.6 g of 2-n-butyl-6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. extractionThis mixture was extracted with ethyl acetate
  4. washThe organic phase was washed twice with 10% aqueous sodium hydroxide solution
  5. customdried
  6. customThe solids obtained
  7. customwere recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-a8dbef27390442189699f5cceb6a732b
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995157B2

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