Sodium Sulfate → 1h-Benzimidazole-6-methanol,1-[(2-chlorophenyl)methyl]-2-methyl-
Reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([C:14](OCC)=[O:15])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:19].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[NH4+].[Li].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([CH2:14][OH:15])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2.66 g of 1-(2-chlorobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole in 20 ml of tetrahydrofuran was slowly added to a solution of 1.54 g of lithium aluminum hydride in 20 ml of tetrahydrofuran at a temperature of from 20 to 25° C. Further, the mixture was stirred at room temperature for 1 hour. Thirty milliliters of tetrahydrofuran were added thereto to dilute the reaction solution. Lithium ammonium hydride was decomposed and solidified with a saturated aqueous solution of sodium sulfate, and the tetrahydrofuran layer was separated. The solvent was distilled off, and the residue was purified through silica-gel column chromatography (eluent: a mixture of chloroform and methanol at a ratio of 9:1) to give 1.45 g of 1-(2-chlorobenzyl)-6-hydroxymethyl-2-methylbenzimidazole.
Workup
- additionto dilute the reaction solution
- customthe tetrahydrofuran layer was separated
- distillationThe solvent was distilled off
- customthe residue was purified through silica-gel column chromatography (eluent
- additiona mixture of chloroform and methanol at a ratio of 9:1)
Sources & evidence
- ORD record
- ord-b9780ffbde374e5eafda12e93553ae47
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06352985B1
Reaction notes
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