Hydrochloric Acid → 4-chloro-1-(4-methoxybutyl)-2-phenyl-1H-imidazole-5-carboxylic acid

HRID 1509546Notes

Reaction equation

HRID 1509546 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:5]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[C:6]=1[CH:7]=[O:8].Cl([O-])=[O:22].[Na+].P([O-])(O)(O)=O.[Na+].Cl>C(O)(C)(C)C.CC(=CC)C>[Cl:1][C:2]1[N:3]=[C:4]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:5]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[C:6]=1[C:7]([OH:22])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 583555004-chloro-1-(4-methoxybutyl)-2-phenyl-1H-imidazole-5-carbaldehyde

Product 1

HCID 583555054-chloro-1-(4-methoxybutyl)-2-phenyl-1H-imidazole-5-carboxylic acidYield 87.6%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

To a solution of 4-chloro-1-(4-methoxybutyl)-2-phenyl-1H-imidazole-5-carbaldehyde (790 mg) in tert-butanol (15 ml) and 2-methyl-2-butene (1.5 ml) was added aqueous solution (4 ml) of sodium chlorite (300 mg) and sodium dihydrogen phosphate (400 mg), and the mixture was stirred at room temperature for 12 hr. 1M Hydrochloric acid was added, and the mixture was adjusted to pH 3, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (730 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7bd30bb1ba81412eaaa7b618a699e990
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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