Benzyl Chloride → 1-Benzyl-2-[2-(4methylpiperazin-1-yl) ethylthio]benzimidazole

HRID 703501Notes

Reaction equation

HRID 703501 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][S:10][C:11]2[NH:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)[CH2:4][CH2:3]1.[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>>[CH2:20]([N:15]1[C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[N:12]=[C:11]1[S:10][CH2:9][CH2:8][N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 221503952-[2-(4-Methylpiperazin-1-yl)ethylthio] benzimidazole

Product 1

HCID 231295371-Benzyl-2-[2-(4methylpiperazin-1-yl) ethylthio]benzimidazole

Procedure

Grams 2 2-[2-(4-methylpiperazin-1-yl)ethylthio] benzimidazole, 0.86 ml benzyl chloride, a 3.5 g aqueous solution containing 1.16 g NaOH and 7.5 ml N,N-dimethylformanide were refluxed for 6 hours, then the solid precipitate was filtered off, and the limpid solution was evaporated almost to dryness. The obtained residue was dissolved in chloroform and water and the extraction was carried out three times; the organic phase was washed, made anhydrous and then evaporated to dryness. The obtained residue was chromatographed on a column eluting with chloroform, methyl alcohol, cyclohexane, ammonium hydroxide (65:15:15:0.1). The fractions, which contained the compound, were evaporated to dryness and the residue which was taken up with boiling petroleum ether (80°-φ° C.) and separated from the insoluble oil, gave, on cooling 0.3 g 1-benzyl-2-[2-4- methylpiperazin-1-ethylthio]benzimidazole melting at 122°-125° C.

Workup

  1. temperaturewere refluxed for 6 hours
  2. filtrationthe solid precipitate was filtered off
  3. customthe limpid solution was evaporated almost to dryness
  4. dissolutionThe obtained residue was dissolved in chloroform
  5. extractionwater and the extraction
  6. washthe organic phase was washed
  7. customevaporated to dryness
  8. customThe obtained residue was chromatographed on a column
  9. washeluting with chloroform, methyl alcohol, cyclohexane, ammonium hydroxide (65:15:15:0.1)
  10. customwere evaporated to dryness
  11. customwas taken up with boiling petroleum ether (80°-φ° C.)
  12. customseparated from the insoluble oil
  13. customgave

Sources & evidence

ORD record
ord-3713bcd3ada74ae68708491e696a33e4
Source dataset
uspto-grants-1991_01
Patent number
US04983620

Reaction notes

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