Chloroacetyl chloride → 2-(3-(5-(Chloromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-b]pyridazine

HRID 251810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 251810
[N:1]1[C:2]([C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2.NO.Cl.CC[N:23](CC)CC.[Cl:28][CH2:29][C:30](Cl)=[O:31]>CCO.C1(C)C=CC=CC=1>[Cl:28][CH2:29][C:30]1[O:31][N:23]=[C:13]([C:12]2[CH:11]=[C:10]([C:2]3[N:1]=[C:9]4[CH:8]=[CH:7][CH:6]=[N:5][N:4]4[CH:3]=3)[CH:17]=[CH:16][CH:15]=2)[N:14]=1

Komponenten

7

Edukt 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 534394773-(Imidazo[1,2-b]pyridazin-2-yl)benzonitrile

Produkt 1

HCID 576868302-(3-(5-(Chloromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-b]pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 0.5 mmol 3-(imidazo[1,2-b]pyridazin-2-yl)benzonitrile, 1 mmol NH2OH.HCl and 1 mmol Et3N in EtOH was stirred at reflux for 4 h then cooled. Excess of solvent was removed in vacuo to afford the crude product. 2-chloroacetyl chloride (2 mmol) was added to the mixture solution of the crude product in Toluene (15 ml) at room temperature and then the mixture was heated to reflux for 5 h. The mixture was concentrated in vacuo and the crude product was purified by column chromatography on silica gel to give the 2-(3-(5-(chloromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-b]pyridazine.

Aufarbeitung

  1. temperatureat reflux for 4 h
  2. temperaturethen cooled
  3. customExcess of solvent was removed in vacuo
  4. customto afford the crude product
  5. temperaturethe mixture was heated
  6. temperatureto reflux for 5 h
  7. concentrationThe mixture was concentrated in vacuo
  8. customthe crude product was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8b97e12a52974da6a2c6dae197eaf1ca
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868001B2

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