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

HRID 2215061
Notes
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Reaction equation

HRID 2215061 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:11]([CH3:19])=[C:12]([C:14]([O:16]CC)=[O:15])[N:13]=1.[Li+].[OH-].O.Cl>C1COCC1.C(OC(=O)C)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[C:11]([CH3:19])=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 3939Lithium HydroxideHCID 11188916ethyl 2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)-5-methyl-1H-imidazole-4-carboxylate

Product 1

HCID 111997572-(2,4-dichlorophenyl)-5-methyl-1-(4-methoxyphenyl)-1H-imidazole-4-carboxylic acidYield 87%

Reagents, catalysts & solvents

2
HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Part B: To a stirred solution of ethyl 2-(2,4-dichlorophenyl)-5-methyl-1-(4-methoxyphenyl)-1H-imidazole-4-carboxylate (8.00 gram, 0.0198 mol) in THF (80 mL) is added LiOH (0.59 gram, 2 molar equivalents) and water (80 mL). The resulting mixture is stirred for 16 hours at 80° C. After cooling to room temperature, HCl (2N solution, 12.3 mL) is added to give an oily precipitate. After addition of water and extraction with ethylacetate, the ethylacetate layer is collected, dried over Na2SO4, filtered and concentrated in vacuo. The residue is crystallised from diisopropyl ether and dried to give 2-(2,4-dichlorophenyl)-5-methyl-1-(4-methoxyphenyl)-1H-imidazole-4-carboxylic acid (4.04 gram, 87% yield) as a pale grey solid. Melting point: 189–191° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. customto give an oily precipitate
  3. customthe ethylacetate layer is collected
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is crystallised from diisopropyl ether
  8. customdried

Sources & evidence

ORD record
ord-98535637c1734d6dbe340367f71b75d8
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07109216B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes