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

HRID 1352654Notes

Reaction equation

HRID 1352654 reaction equation
[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13]C(C#N)=[CH:11][C:10]=3[O:17][CH3:18])[NH:8][C:4]=2[CH:3]=1.[OH-:22].[Na+].[CH2:24]([OH:26])[CH3:25]>>[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:25]([C:24]([OH:22])=[O:26])=[CH:11][C:10]=3[O:17][CH3:18])[NH:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 211011705,6-Dichloro-2-(4-cyano-2-methoxyphenyl)benzimidazole

Product 1

HCID 211011665,6-Dichloro-2-(4-carboxy-2-methoxyphenyl)benzimidazoleYield 46%

Procedure

A solution of 5,6-dichloro-2-(4-cyano-2-methoxyphenyl)benzimidazole, prepared as described in Preparation 5, in ethanol (50 ml) and 2N NaOH (15 ml) was refluxed for 16 h. Solvent was removed under reduced pressure and the residue was acidified with 37% HCl (10 ml), stirred for 1 h. The solid was filtered, washed with water (50 ml), dried at 50° C. under vacuum to give 0.92 g of the title compound (yield 46%), mp>250° C.

Workup

  1. customSolvent was removed under reduced pressure
  2. filtrationThe solid was filtered
  3. washwashed with water (50 ml)
  4. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-3445a8b6f87740ee933c94b4d448fb7d
Source dataset
uspto-grants-2007_05
Patent number
US07220769B2

Reaction notes

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