Ethanol → 5,6-Dichloro-2-(4-carboxy-2-ethoxyphenyl)benzimidazole hydrochloride

HRID 1352661Notes

Reaction equation

HRID 1352661 reaction equation
Cl.[Cl:2][C:3]1[C:22]([Cl:23])=[CH:21][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14]C(C#N)=[CH:12][C:11]=3[O:18][CH2:19][CH3:20])[NH:9][C:5]=2[CH:4]=1.[OH-:24].[Na+].[CH2:26]([OH:28])[CH3:27]>>[ClH:2].[Cl:2][C:3]1[C:22]([Cl:23])=[CH:21][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][C:27]([C:26]([OH:24])=[O:28])=[CH:12][C:11]=3[O:18][CH2:19][CH3:20])[NH:9][C:5]=2[CH:4]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 211011675,6-Dichloro-2-(4-cyano-2-ethoxyphenyl)benzimidazole hydrochloride

Product 1

HCID 211011635,6-Dichloro-2-(4-carboxy-2-ethoxyphenyl)benzimidazole hydrochlorideYield 70%

Procedure

A mixture of 5,6-dichloro-2-(4-cyano-2-ethoxyphenyl)benzimidazole hydrochloride (16.3 g, 44.2 mmol), prepared as in Preparation 12, 32% NaOH (40 ml) in ethanol (100 ml) was refluxed for 8 h. After cooling to room temperature the organic solvent was removed under vacuum and the aqueous phase was acidified with 37% HCl, stirred for 1 h. The solid was filtered, washed with water (100 ml) and dried at 50° C. under vacuum to give 12 g of the title compound as a light brown powder (yield 70%), mp>250° C.

Workup

  1. temperaturewas refluxed for 8 h
  2. customwas removed under vacuum
  3. filtrationThe solid was filtered
  4. washwashed with water (100 ml)
  5. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-283fbcb77ef7408faa690bc1d65e7bd0
Source dataset
uspto-grants-2007_05
Patent number
US07220769B2

Reaction notes

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