Sodium Sulfate → HCID 22620335, compound

HRID 840774Notes

Reaction equation

HRID 840774 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([C:17](OCC)=[O:18])[CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[CH3:22])=[CH:3][CH:2]=1.[H-].[Li+].[Al+3].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([CH2:17][OH:18])[CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[CH3:22])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 18680890HCID 18680890, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 22620335HCID 22620335, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Tetrahydrofuran (20 ml) solution of 1-(biphenyl-4-ylmethyl)-6-ethoxycarbonyl-2-methylbenzimidazole (5.30 g) is slowly added to a tetrahydrofuran (20 ml) solution of aluminum lithium hydride (2.17 g). Further, the solution is stirred for one hour at room temperature. By adding tetrahydrofuran (30 ml), the reaction solution is diluted. By adding a saturated sodium sulfate aqueous solution, the aluminum lithium hydride is decomposed, solidified and the tetrahydrofuran layer is separated. The solvent is removed through evaporation. Purification using silica gel column chromatography produced 1-(biphenyl-4-ylmethyl)-6-hydroxymethyl-2-methylbenzimidazole (3.72 g). 1H-NMR (CDCl3, δ): 2.59 (3H, s), 4.78 (2H, s), 5.37 (2H. s), 7.11 (2H, d, J=8.3 Hz), 7.24 (1H, d, J=8.3 Hz), 7.30-7.37 (2H, m), 7.42 (2H, t), 7.51-7.56 (4H, m), 7.70 (1H, d, J=8.2 Hz).

Workup

  1. additionthe reaction solution is diluted
  2. customthe tetrahydrofuran layer is separated
  3. customThe solvent is removed through evaporation
  4. customPurification

Sources & evidence

ORD record
ord-78a86ff9eafc4b68b395cbbddde028d8
Source dataset
uspto-grants-2002_04
Patent number
US06369092B1

Reaction notes

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