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

HRID 1788927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1788927
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-5cf67d07029a4e36b2dd22857e9ca32e
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04686227

Notizen zur Reaktion

Wird geladen…