Hydrochloric Acid → 2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzoic acid

HRID 1433219Notes

Reaction equation

HRID 1433219 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:30]=[CH:29][C:13]2[NH:14][C:15]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[N:16][C:12]=2[CH:11]=1.CO.[OH-].[Li+].Cl>CCOC(C)=O.O>[F:28][C:25]([F:26])([F:27])[C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:17][C:15]2[NH:14][C:13]3[CH:29]=[CH:30][C:10]([C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:3]([OH:31])=[O:2])=[CH:11][C:12]=3[N:16]=2)=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 178497613HCID 178497613, compound

Product 1

HCID 1785242792-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzoic acidYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzoic acid methyl ester (0.494 g, 1.16 mmol) in mixed solvent (30 mL, MeOH: H2O=3:1) was added lithium hydroxide (0.166 g, 6.95 mmol). After stirring for 12 hours, the reaction mixture was diluted with EtOAc and acidified by aqueous 3N HCl. The organic layer was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to afford the title compound as a white solid (0.435 g, 91%).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-056f81d3b12b45e8b7dd059787508695
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

Loading…