Lithium hydroxide, monohydrate → 6-chloro-5-(cyclopropylcarbamoyl)-1H-benzimidazole-2-carboxylic acid

HRID 514259Notes

Reaction equation

HRID 514259 reaction equation
[Cl:1][C:2]1[C:3]([C:15](=[O:20])[NH:16][CH:17]2[CH2:19][CH2:18]2)=[CH:4][C:5]2[N:9]=[C:8]([C:10]([O:12]C)=[O:11])[NH:7][C:6]=2[CH:14]=1.O.[OH-].[Li+]>O1CCCC1.O>[Cl:1][C:2]1[C:3]([C:15](=[O:20])[NH:16][CH:17]2[CH2:18][CH2:19]2)=[CH:4][C:5]2[N:9]=[C:8]([C:10]([OH:12])=[O:11])[NH:7][C:6]=2[CH:14]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68292997methyl 6-chloro-5-(cyclopropylcarbamoyl)-1H-benzimidazole-2-carboxylate

Product 1

HCID 682930886-chloro-5-(cyclopropylcarbamoyl)-1H-benzimidazole-2-carboxylic acidYield 84.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-chloro-5-(cyclopropylcarbamoyl)-1H-benzimidazole-2-carboxylate (2.1 g, 7.2 mmol) in tetrahydrofuran (50 ml) was added dropwise, at 0° C., a solution of lithium hydroxide monohydrate (0.6 g, 14.3 mmol) in water (25 ml). The reaction mixture was stirred at this temperature for 14 h. After removing the tetrahydrofuran under reduced pressure, the aqueous solution was acidified with hydrochloric acid (2 M). The precipitated solid was filtered off with suction. 1.7 g (81% of theory) of 6-chloro-5-(cyclopropylcarbamoyl)-1H-benzimidazole-2-carboxylic acid were obtained.

Workup

  1. customAfter removing the tetrahydrofuran under reduced pressure
  2. filtrationThe precipitated solid was filtered off with suction

Sources & evidence

ORD record
ord-e66b9b5c3dee451b853ad6def0848b35
Source dataset
uspto-grants-2015_08
Patent number
US09107411B2

Reaction notes

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