Lithium Hydroxide → HCID 11417294, compound

HRID 1296359Notes

Reaction equation

HRID 1296359 reaction equation
[Li+].[OH-].C([O:5][C:6]([C:8]1[N:9]=[C:10]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[Cl:27])[N:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH:12]=1)=[O:7])C>CO>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([N:11]2[CH:12]=[C:8]([C:6]([OH:7])=[O:5])[N:9]=[C:10]2[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[Cl:27])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 11463589ethyl 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-1H-imidazole-4-carboxylate

Product 1

HCID 11417294HCID 11417294, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of LiOH (6.36 g, 152 mmol) was added to a suspension of 1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester I-7c (30 g, 75.8 mmol) in methanol (380 ml). The reaction mixture was heated to reflux for 1 h and then cooled to room temperature. Most of the solvent was removed in vacuo, and the residue was diluted with water and acidified with 3N HCl. The red-brown precipitate was collected by filtration and triturated with 100 ml ethyl acetate/hexanes (20:80) to afford 1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid I-7d (26.3 g, 94%) as a pale yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. customMost of the solvent was removed in vacuo
  4. additionthe residue was diluted with water
  5. filtrationThe red-brown precipitate was collected by filtration
  6. customtriturated with 100 ml ethyl acetate/hexanes (20:80)

Sources & evidence

ORD record
ord-26c95afc83494e6494593531b2553c01
Source dataset
uspto-grants-2007_07
Patent number
US07247628B2

Reaction notes

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