Sodium Hydroxide → HCID 58374090, compound

HRID 1948549Notes

Reaction equation

HRID 1948549 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[C:11]([C:17]([O:19]CC)=[O:18])[N:10]=[CH:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CCO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([F:16])([F:14])[F:15])=[C:11]([C:17]([OH:19])=[O:18])[N:10]=[CH:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11034512HCID 11034512, compound

Product 1

HCID 58374090HCID 58374090, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 1-(4-chlorophenyl)-5-(trifluoromethyl)-1H-imidazole-4-carboxylate (800 mg, 2.51 mmol) in EtOH (20 mL) was added a predissolved solution of sodium hydroxide (1004 mg, 25.1 mmol) in Water (5.00 mL). The reaction was stirred overnight at room temperature. The next day, the reaction was concentrated in vacuo, acidified with dilute HCl and extracted 2×EtOAc. The organic layers were dried over MgSO4, filtered, and concentrated to give 1-(4-chlorophenyl)-5-(trifluoromethyl)-1H-imidazole-4-carboxylic acid (400 mg, 1.376 mmol, 54.8% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.3 (1H, br s), 8.19 (1H, dd), 7.68 (2H, d), 7.72 (2H, d).

Workup

  1. concentrationThe next day, the reaction was concentrated in vacuo
  2. extractionextracted 2×EtOAc
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f49e8f03cd3c43f1a7daa834639b7dac
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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