Hydrochloric Acid → 1-(4-bromobenzyl)-1H-benzo[d]imidazole-5-carboxylic acid

HRID 626404Notes

Reaction equation

HRID 626404 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([O:18]C)=[O:17])=[CH:15][C:10]=3[N:9]=[CH:8]2)=[CH:4][CH:3]=1.[Li+].[OH-].Cl>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([OH:18])=[O:17])=[CH:15][C:10]=3[N:9]=[CH:8]2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89588597methyl 1-(4-bromobenzyl)-1H-benzo[d]imidazole-5-carboxylate

Product 1

HCID 285381601-(4-bromobenzyl)-1H-benzo[d]imidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of methyl 1-(4-bromobenzyl)-1H-benzo[d]imidazole-5-carboxylate (650 mg, 1.88 mmol) and LiOH (150 mg, 3.76 mmol) in Methanol (10 mL) and 1120 (5 mL) was stirred at RT overnight. Then the methanol was removed under the reduced pressure to get a residue, pH was adjusted to 7 with 3N HCl to give a large number of precipitation, then filtered and the filter cake was washed by water (5 mL×2), dried under vacuum to give the titled compound.

Workup

  1. customThen the methanol was removed under the reduced pressure
  2. customto get a residue, pH
  3. customto give
  4. customa large number of precipitation
  5. filtrationfiltered
  6. washthe filter cake was washed by water (5 mL×2)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-e4eec61558024050a058c909a0d2f5a5
Source dataset
uspto-grants-2016_04
Patent number
US09309227B2

Reaction notes

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