Hydrochloric Acid → 4-({[(4-Methyl-3-fluorophenyl)amino]carbonyl}amino)-1-methyl-1H-imidazole-2-carboxylic Acid

HRID 499907Notes

Reaction equation

HRID 499907 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13]2[N:14]=[C:15]([C:19]([O:21]CC)=[O:20])[N:16]([CH3:18])[CH:17]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[OH-].[Na+].Cl>C(O)C.O1CCCC1>[CH3:8][C:7]1[CH:6]=[CH:5][C:4]([NH:9][C:10]([NH:12][C:13]2[N:14]=[C:15]([C:19]([OH:21])=[O:20])[N:16]([CH3:18])[CH:17]=2)=[O:11])=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11709531Ethyl 4-({[(3-fluoro-4-methylphenyl)amino]carbonyl}amino)-1-methyl-1H-imidazole-2-carboxylate

Product 1

HCID 594217444-({[(4-Methyl-3-fluorophenyl)amino]carbonyl}amino)-1-methyl-1H-imidazole-2-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

690 mg (2.15 mmol) of ethyl 4-({[(3-fluoro-4-methylphenyl)amino]carbonyl}amino)-1-methyl-1H-imidazole-2-carboxylate are suspended in 5 ml of ethanol and 12 ml of tetrahydrofuran. While cooling in ice, 2 ml (25 mmol) of 50% strength aqueous sodium hydroxide solution are added. The reaction mixture is stirred at room temperature overnight and then, while cooling in ice, acidified with 1N hydrochloric acid. The solution is extracted with dichloromethane. The organic phase is concentrated in vacuo.

Workup

  1. temperatureWhile cooling in ice
  2. temperaturewhile cooling in ice
  3. extractionThe solution is extracted with dichloromethane
  4. concentrationThe organic phase is concentrated in vacuo

Sources & evidence

ORD record
ord-527c7153dc6d4d85b044ecaa620db8f6
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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