Hydrochloric Acid → 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylic acid

HRID 1428990Notes

Reaction equation

HRID 1428990 reaction equation
[CH3:1][C:2]1[N:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4]([CH3:11])=[C:5]([C:7]([O:9]C)=[O:8])[N:6]=1.[Li+].[OH-].Cl>C1COCC1.O>[CH3:1][C:2]1[N:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4]([CH3:11])=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 14003955methyl 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylate

Product 1

HCID 545792222,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylic acidYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Part D: To a magnetically stirred solution of methyl 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylate (8.0 gram, 0.035 mol) in THF (100 ml) was added a solution of LiOH (1.68 gram) in water (100 ml). The resulting mixture was heated at 70° C. for 16 hours, allowed to attain room temperature and acidified with 2 molar equivalents of a 1N HCl solution. The formed precipitate was collected to give crude 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylic acid (7.0 gram, 93% yield). 1H-NMR (400 MHz, DMSO-d6): 2.31 (s, 3H), 2.43 (s, 3H), 7.56-7.61 (m, 2H), 7.66-7.71 (m, 3H).

Workup

  1. customto attain room temperature
  2. customThe formed precipitate was collected

Sources & evidence

ORD record
ord-76e6fa856221452c888966645b4d221a
Source dataset
uspto-grants-2015_01
Patent number
US08937184B2

Reaction notes

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