Water → 2-((3-methyl-4-(3-(N,N-bis(2-hydroxyethyl)amino)propylthio)-2-pyridyl)methylthio)-1H-benzimidazole
Reaction equation
[CH3:1][C:2]1[C:3]([CH2:13][S:14][C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)=[N:4][CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][CH2:11][NH2:12].[CH2:24](Br)[CH2:25][OH:26].[C:28](=[O:31])([O-])[O-].[K+].[K+].O.[CH3:35]N(C)C=O>>[CH3:1][C:2]1[C:3]([CH2:13][S:14][C:15]2[NH:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[N:4][CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:35][CH2:28][OH:31])[CH2:24][CH2:25][OH:26]Participants
6
Reactant 5
Product 1
Procedure
2-((3-Methyl-4-(3-aminopropylthio)-2-pyridyl)methylthio)-1H-benzimidazole (2.0 g) was dissolved in dimethylformamide (20 ml) and thereto were added ethylene bromohydrin (1.52 g) and potassium carbonate (2.0 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-(3-(N,N-bis(2-hydroxyethyl)amino)propylthio)- 2-pyridyl)methylthio)-1H-benzimidazole as a pale yellow oil.
Workup
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled away under reduced pressure
- washeluted with chloroform-methanol
Sources & evidence
- ORD record
- ord-a8c9c7d6ef7a4977aeb400f622220b9d
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05504082
Reaction notes
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