Benzaldehyde → 2-((3-Methyl-4-(2-benzylaminoethylthio)pyridin-2-yl)methylthio)-1H-benzimidazole

HRID 52148Notes

Reaction equation

HRID 52148 reaction equation
[CH3:1][C:2]1[C:3]([CH2:12][S:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]=2)=[N:4][CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][NH2:11].[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[C:3]([CH2:12][S:13][C:14]2[NH:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)=[N:4][CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][NH:11][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 19962990HCID 19962990, compound

Product 1

HCID 199630842-((3-Methyl-4-(2-benzylaminoethylthio)pyridin-2-yl)methylthio)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-((3-Methyl-4-(2-aminoethylthio)-2-pyridyl)methylthio)-1H-benzimidazole (8.5 g) was dissolved in ethanol and thereto was added benzaldehyde (2.8 g). The mixture was stirred at 50°-55° C. for 5 hours and sodium borohydride (0.98 g) was added thereto under ice-cooling. The mixture was stirred at room temperature for 2 hours. After the completion of the reaction, ethanol was distilled away and the residue was eluted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and the solvent was distilled away. The residue was purified by column chromatography to give 2-((3-methyl-4-(2-benzylaminoethylthio)-2-pyridyl)methylthio)-1H-benzimidazole.

Workup

  1. temperatureunder ice-cooling
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. distillationwas distilled away
  4. washthe residue was eluted with chloroform
  5. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8c82e6f3daed4d1f915850327fa424c5
Source dataset
uspto-grants-1997_04
Patent number
US05616581

Reaction notes

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