Hydrochloric Acid → HCID 11417294, compound

HRID 2112987Notes

Reaction equation

HRID 2112987 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[N:10]=[C:9]2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[CH:4][CH:3]=1.[Li+].[OH-].O.Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[N:10]=[C:9]2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 3939Lithium HydroxideHCID 11463589HCID 11463589, compound

Product 1

HCID 11417294HCID 11417294, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a magnetically stirred solution of ethyl 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-1H-imidazole-4-carboxylate (18.44 g, 0.0466 mol) in THF (240 ml) was added LiOH (2.24 g, 0.0932 mol) and H2O (240 ml). The resulting mixture was stirred at 50° C. for 16 h to give a clear solution. After cooling to room temperature, HCl (1 N solution, 95 ml) and H2O (240 ml) were added to give a precipitate which was collected by filtration, washed with water and dried in vacuo to give 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-1H-imidazole-4-carboxylic acid (16.83 g, 98% yield), mp 138-142° C. (decomposition); 1H-NMR (600 MHz, DMSO-d6) δ 7.08 (br d, J=8 Hz, 2H), 7.31-7.37 (m, 4H), 7.45 (d, J=8 Hz, 1H), 7.96 (s, 1H); 13C-NMR (150 MHz, DMSO-d6) δ 126.87, 127.85, 127.91, 128.47, 129.36, 129.66, 133.56, 133.99, 134.44, 134.49, 135.54, 135.99, 143.77, 163.67.

Workup

  1. customto give a clear solution
  2. temperatureAfter cooling to room temperature
  3. customto give a precipitate which
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e030816bd52d4a20b37e05ee6e5fb071
Source dataset
uspto-grants-2009_04
Patent number
US07524867B2

Reaction notes

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