Sodium Hydroxide → [2-(5-chlorothiophen-2-yl)-1H-benzimidazol-5-yl]acetic acid

HRID 230732Notes

Reaction equation

HRID 230732 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[S:8][C:7]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([CH2:18][C:19]([O:21]CC)=[O:20])=[CH:17][C:11]=3[N:10]=2)=[CH:6][CH:5]=1>CO>[Cl:3][C:4]1[S:8][C:7]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([CH2:18][C:19]([OH:21])=[O:20])=[CH:17][C:11]=3[N:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178470643HCID 178470643, compound

Product 1

HCID 178525013[2-(5-chlorothiophen-2-yl)-1H-benzimidazol-5-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.2 34.7 ml of aqueous 1 N sodium hydroxide solution are added to a solution of 10.1 g (about 20.5 mmol) of ethyl [2-(5-chlorothiophen-2-yl)-1H-benzimidazol-5-yl]acetate in 70 ml of methanol, and the mixture is stirred at room temperature for 3 days. The reaction mixture is evaporated, and the residue is taken up in 25 ml of water. A pH of 4.5 is set by addition of conc. hydrochloric acid. The resultant precipitate is filtered off, washed with water and dried, giving [2-(5-chlorothiophen-2-yl)-1H-benzimidazol-5-yl]acetic acid as a yellowish solid; ESI 293.

Workup

  1. customThe reaction mixture is evaporated
  2. additionA pH of 4.5 is set by addition of conc. hydrochloric acid
  3. filtrationThe resultant precipitate is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-7b69e652f31845f9ba00889a84ca3bca
Source dataset
uspto-grants-2009_07
Patent number
US07566789B2

Reaction notes

Loading…