Sodium Hydroxide → 8-(5-Methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline

HRID 1088813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088813
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8](Cl)[NH:9][C:5]=2[CH:4]=1.NC(N)=[S:15].Cl.[CH3:18][N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[CH2:29]Cl)[CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>O.C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([S:15][CH2:29][C:27]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:28]=3[N:19]([CH3:18])[CH2:20][CH2:21][CH2:22]4)[NH:9][C:5]=2[CH:4]=1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 5191972-Chloro-5-methoxy-1H-benzimidazoleHCID 2723790ThioureaHCID 221617911-Methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline hydrochloride

Produkt 1

HCID 150533328-(5-Methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinolineAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

5-Methoxy-2-chlorobenzimidazole (0.55 g), thiourea (0.2 g) and ethanol (10 ml) were refluxed for 2 hours. To the reaction mixture was added a solution of 1-methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline hydrochloride (0.51 g) and sodium hydroxide (0.3 g) in water (5 ml) and the mixture was refluxed for 5 hours. After completion of the reaction, ethanol was distilled off and water was added to the resulting residue, and the mixture was extracted with chloroform. After drying over anhydrous magnesium sulfate, chloroform was distilled off. The resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (4:1)] to give 8-(5-methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline (0.62 g).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 5 hours
  2. distillationwas distilled off
  3. additionwater was added to the resulting residue
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialAfter drying over anhydrous magnesium sulfate, chloroform
  6. distillationwas distilled off
  7. customThe resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (4:1)]

Quellen und Nachweise

ORD-Eintrag
ord-df696adb185e4742983da6ba8101c272
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04963566

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