Hydrochloric Acid → 1-(4-Benzyloxyphenyl)-2-(2,4-dichlorophenyl)-5-methyl-1H-imidazole-4-carboxylic acid

HRID 1715093Notes

Reaction equation

HRID 1715093 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])[N:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[C:10]=1[CH3:11])=[O:5])C.[OH-].[K+].Cl>CO.O>[CH2:19]([O:18][C:15]1[CH:14]=[CH:13][C:12]([N:9]2[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[N:7]=[C:8]2[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])=[CH:17][CH:16]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 594655051-(4-Benzyloxyphenyl)-2-(2,4-dichlorophenyl)-5-methyl-1H-imidazole-4-carboxylic acid ethyl ester

Product 1

HCID 594655061-(4-Benzyloxyphenyl)-2-(2,4-dichlorophenyl)-5-methyl-1H-imidazole-4-carboxylic acidYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 1-(4-benzyloxyphenyl)-2-(2,4-dichlorophenyl)-5-methyl-1H-imidazole-4-carboxylic acid ethyl ester, from Ex. 1, Step 2 (3.62 g, 7.5 mmol) in 60 ml methanol was added potassium hydroxide (4.05 g, 72 mmol) in water (20 ml), and the reaction mixture was refluxed for 2 hours. The mixture was cooled to room temperature, acidified to pH˜2 with 1 M HCl and extracted with ethyl acetate (2×200 ml). The combined organic phases were dried (Na2SO4), filtered and concentrated to give 3.38 g (99%) of the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. extractionextracted with ethyl acetate (2×200 ml)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-31cc549f30374d26a733e15cb7959df2
Source dataset
uspto-grants-2010_09
Patent number
US07799804B2

Reaction notes

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