Ethanol → 7-Chloro-3-(1-imidazolylmethyl)-2-methylimidazo[2,1-a]isoquinoline

HRID 649152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 649152
C(O)C.COS([O-])(=O)=O.[Cl:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][N:15]1[C:23]([CH2:24][N+](C)(C)C)=[C:22]([CH3:29])[N:21]=[C:16]12.[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1>CS(C)=O>[Cl:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][N:15]1[C:23]([CH2:24][C:31]3[NH:30][CH:34]=[CH:33][N:32]=3)=[C:22]([CH3:29])[N:21]=[C:16]12

Komponenten

5

Edukt 3

HCID 702EthanolHCID 795ImidazoleHCID 138218647-Chloro-2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline methylsulfate

Produkt 1

HCID 704198067-Chloro-3-(1-imidazolylmethyl)-2-methylimidazo[2,1-a]isoquinolineAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Ethanol (50 ml) was added to a mixture of 7-chloro-2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline methylsulfate (2.3 g) and imidazole (0.95 g) in dimethyl sulfoxide (20 ml) and heated at 100° C. with stirring for 5 hours. After the removal of ethanol by distillation, the residue was poured into water. The resulting precipitates were collected by filtration, dried and recrystallized from ethyl acetate. The obtained crystals were chromatographed on silica gel (16 g) with a mixture of chloroform and methanol (10:1) as an eluent. The eluates were evaporated in vacuo and the residual solid was recrystallized from ethyl acetate to give 7-chloro-3-(1-imidazolylmethyl)-2-methylimidazo[2,1-a]isoquinoline (0.7 g).

Aufarbeitung

  1. customAfter the removal of ethanol
  2. distillationby distillation
  3. additionthe residue was poured into water
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. customdried
  7. customrecrystallized from ethyl acetate
  8. customThe obtained crystals were chromatographed on silica gel (16 g) with a mixture of chloroform and methanol (10:1) as an eluent
  9. customThe eluates were evaporated in vacuo
  10. customthe residual solid was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d3fcd37c1fb04a1a9f81100b2f53b7e0
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04738967

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