Benzaldehyde → HCID 178432167, compound

HRID 1030516Notes

Reaction equation

HRID 1030516 reaction equation
[NH2:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1.CO.O>[CH2:12]([NH:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 4311764Sodium borohydrideHCID 178432166HCID 178432166, compound

Product 1

HCID 178432167HCID 178432167, compoundYield 1.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 3.8 g (0.026 mol) 4-amino-2-methylbenzimidazole, 2.7 g (0.026 mol) benzaldehyde and 0.05 g paratoluene sulfonic acid in 250 ml toluene was refluxed and the water formed was separated during 20 h. Upon cooling the volatiles were removed under reduced pressure. The residue obtained was suspended in 150 ml methanol and 1.8 g (0.048 mol) NaBH4 was added. The mixture was stirred at room temperature for 2 h and methanol was removed under reduced pressure. The residue was dissolved in methylene chloride, washed with water and dried (Na2SO4). After filtration, methylene chloride was removed under reduced pressure. Chromatography on silica gel and elution with methylene chloride:methanol (10:1) gave 0.1 g (0.00042 mol) of 4-benzylamino-2-methyl benzimidazole

Workup

  1. temperaturewas refluxed
  2. customwas separated during 20 h
  3. temperatureUpon cooling the volatiles
  4. customwere removed under reduced pressure
  5. customThe residue obtained
  6. custommethanol was removed under reduced pressure
  7. dissolutionThe residue was dissolved in methylene chloride
  8. washwashed with water
  9. dry with materialdried (Na2SO4)
  10. filtrationAfter filtration, methylene chloride
  11. customwas removed under reduced pressure
  12. washChromatography on silica gel and elution with methylene chloride:methanol (10:1)

Sources & evidence

ORD record
ord-cc54039658e04c728d79add1bdba706f
Source dataset
uspto-grants-1992_04
Patent number
US05106862

Reaction notes

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