Sodium Hydroxide → HCID 9844690, compound

HRID 440580Notes

Reaction equation

HRID 440580 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH:17]([C:24]([O:26]CC)=[O:25])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)[C:7]2[CH:29]=[CH:30][CH:31]=[C:32]([CH3:33])[C:6]=2[N:5]=1)[CH2:2][CH3:3].[OH-].[Na+]>C(O)C>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH:17]([C:24]([OH:26])=[O:25])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:15]=2)[C:7]2[CH:29]=[CH:30][CH:31]=[C:32]([CH3:33])[C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53656677HCID 53656677, compound

Product 1

HCID 9844690HCID 9844690, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

500 mg (1.1 mMol) of 2-n-propyl-4-methyl-1-[4-[(α-ethoxycarbonyl)benzyloxy]benzyl]benzimidazole are dissolved in 10 ml of ethanol and mixed with 10 ml of 1N sodium hydroxide solution. The mixture is stirred at ambient temperature for 30 minutes. Then the mixture is concentrated by evaporation and taken up in water. The solution is acidified by the addition of glacial acetic acid. The precipitate formed is suction filtered, washed with water until neutral and dried. The crude product is taken up in methylene chloride and purified over a silica gel column (particle size 0.063-0.02 mm), using as eluant a mixture of methylene chloride and methanol (19: 1). The uniform fractions are concentrated by evaporation in vacuo and the residue is triturated with hexane/ether and suction filtered.

Workup

  1. concentrationThen the mixture is concentrated by evaporation
  2. additionThe solution is acidified by the addition of glacial acetic acid
  3. customThe precipitate formed
  4. filtrationfiltered
  5. washwashed with water until neutral and
  6. customdried
  7. custompurified over a silica gel column (particle size 0.063-0.02 mm)
  8. additiona mixture of methylene chloride and methanol (19: 1)
  9. concentrationThe uniform fractions are concentrated by evaporation in vacuo
  10. customthe residue is triturated with hexane/ether and suction
  11. filtrationfiltered

Sources & evidence

ORD record
ord-7437d7baa4dc472abf4a04f7e80dc7c6
Source dataset
uspto-grants-1996_05
Patent number
US05519138

Reaction notes

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