Water → 2-((3-methyl-4-(2-(N,N-bis(2-hydroxyethyl)amino)ethylthio)-2-pyridyl)methylthio)-1H-benzimidazole

HRID 1720056Notes

Reaction equation

HRID 1720056 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].[CH2:23](Br)[CH2:24][OH:25].[C:27](=[O:30])([O-])[O-].[K+].[K+].O.[CH3:34]N(C)C=O>>[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][N:11]([CH2:34][CH2:27][OH:30])[CH2:23][CH2:24][OH:25]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 19962990HCID 19962990, compound

Product 1

HCID 199630552-((3-methyl-4-(2-(N,N-bis(2-hydroxyethyl)amino)ethylthio)-2-pyridyl)methylthio)-1H-benzimidazole

Procedure

2-((3-Methyl-4-(2-aminoethylthio)-2-pyridyl)methylthio)-1H-benzimidazole (2.0 g) was dissolved in dimethylformamide (20 ml) and thereto were added ethylene bromohydrin (1.59 g) and potassium carbonate (2.1 g). The mixture was stirred at 70°-80° C. for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was distilled away under reduced pressure. The residue was subjected to column chromatography and eluted with chloroform-methanol to give 2-((3-methyl-4-(2-(N,N-bis(2-hydroxyethyl)amino)ethylthio)-2-pyridyl)methylthio)-1H-benzimidazole as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. washeluted with chloroform-methanol

Sources & evidence

ORD record
ord-e971c079dc2640949558c5cfe66d3794
Source dataset
uspto-grants-1996_04
Patent number
US05504082

Reaction notes

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