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

HRID 324734Notes

Reaction equation

HRID 324734 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fa9641fcd98f43029021fdac50831631
Source dataset
uspto-grants-2001_04
Patent number
US06218547B1

Reaction notes

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