Methanol → 5-Acetyl-1-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]benzimidazole

HRID 49817

Reaktionsgleichung

Reaktionsgleichung von HRID 49817
[C:1]([C:4]1[CH:23]=[CH:22][C:7]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH2:20][N:19]([CH3:21])[CH2:18][CH2:17][CH:16]=3)[CH:10]=2)=[C:6]([N+:24]([O-])=O)[CH:5]=1)(=[O:3])[CH3:2].O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].[Cl-].[NH4+].[CH3:41]O>C(O)=O>[C:1]([C:4]1[CH:23]=[CH:22][C:7]2[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]4[CH2:20][N:19]([CH3:21])[CH2:18][CH2:17][CH:16]=4)[CH:10]=3)[CH:41]=[N:24][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 73972Sodium sulfide nonahydrateHCID 227418634-acetyl-N-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]-2-nitroaniline

Produkt 1

HCID 227419115-Acetyl-1-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

A mixture of 4-acetyl-N-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]-2-nitroaniline (5) (1 g, 3 mmol), sodium sulfide nonahydrate (4.32 g, 18 mmol) and ammonium chloride (0.96 g, 18 mmol) in methanol (50 ml) was heated to reflux over night. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic phase was dried over sodium sulfate and concentrated to leave an oil (m/e: 321) which was stirred in formic acid (10 ml) at 80° C. for 4 hours. The resulting mixture was concentrated under reduced pressure. The residue was dissolved in water and filtered. The filtrate was rendered alkaline by addition of solid sodium carbonate and extracted with ethyl acetate. This extract was dried over sodium sulfate. Evaporation of the solvent left 5-acetyl-1-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]benzimidazole (7) as an oil. Yield: 0.5 g (50%), m/e: 331. A minor sample of this oil was dissolved in ethanol and precipitated as the hydrochloride by addition of hydrogen chloride in diethyl ether. Mp 227-233° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux over night
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and water
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. customto leave an oil (m/e: 321) which
  8. concentrationThe resulting mixture was concentrated under reduced pressure
  9. dissolutionThe residue was dissolved in water
  10. filtrationfiltered
  11. additionby addition of solid sodium carbonate
  12. extractionextracted with ethyl acetate
  13. dry with materialThis extract was dried over sodium sulfate
  14. customEvaporation of the solvent
  15. waitleft 5-acetyl-1-[3-(1-methyl-1,2,3,6-tetrahydropyrid-5-yl)phenyl]benzimidazole (7) as an oil
  16. dissolutionA minor sample of this oil was dissolved in ethanol
  17. customprecipitated as the hydrochloride by addition of hydrogen chloride in diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-51d9cb00c8fe40ef8da59ceca02c1ed8
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710044B2

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