Hydrochloric Acid → Sodium Chloride

HRID 592331Notes

Reaction equation

HRID 592331 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]3[NH:14][C:15](=[O:22])[N:16]([CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[C:12]=3[CH:11]=[C:10]([C:23]([O:25]C)=[O:24])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+:28].[ClH:29]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]3[NH:14][C:15](=[O:22])[N:16]([CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[C:12]=3[CH:11]=[C:10]([C:23]([OH:25])=[O:24])[CH:9]=2)=[CH:4][CH:3]=1.[Cl-:29].[Na+:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 66690107Methyl 7-(4-fluorophenyl)-3-(2-hydroxy-2-methylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazole-5-carboxylate

Product 2

HCID 5234Sodium ChlorideYield 982.1%HCID 666901397-(4-Fluorophenyl)-3-(2-hydroxy-2-methylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 7-(4-fluorophenyl)-3-(2-hydroxy-2-methylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazole-5-carboxylate (80.0 mg, 0.223 mmol) in MeOH (0.446 mL) was added sodium hydroxide (0.446 mL, 1M, 0.446 mmol). Reaction heated in the microwave at 100° C. for 15 min. More sodium hydroxide (0.446 mL, 1M, 0.446 mmol) added and heated an additional 20 min in the microwave at 100° C. HCl (0.446 mL, 2M in ether, 0.892 mmol) was added and the reaction mixture was concentrated to give the title compound with four equivalents of sodium chloride (128 mg): LC-MS [M+1]=345.3.

Workup

  1. customReaction
  2. temperatureheated an additional 20 min in the microwave at 100° C
  3. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-c433d0da69a548df9a4ed10db856b054
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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