Lithium Hydroxide → HCID 21949014, compound

HRID 1025657Notes

Reaction equation

HRID 1025657 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[C:10]([CH3:18])=[C:11]([C:13]([O:15]CC)=O)[N:12]=2)=[CH:4][CH:3]=1.[Li+].[OH-].O=S(Cl)[Cl:31]>O.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[C:10]([CH3:18])=[C:11]([C:13]([Cl:31])=[O:15])[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 24386Thionyl ChlorideHCID 11292764HCID 11292764, compound

Product 1

HCID 21949014HCID 21949014, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

Part B: Ethyl 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-5-methyl-1H-imidazole-4-carboxylate (0.250 gram, 0.61 mmol) and LiOH (0.052 gram, 2.17 mmol) are dissolved in H2O/THF (1:1 (v/v); 50 mL) and stirred at 50° C. for one hour. The mixture is concentrated to give crude 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-5-methyl-1H-imidazole-4-carboxylic acid. To this mixture is added SOCl2 (50 mL) and the resulting mixture is heated at reflux temperature for 1 hour. The mixture is concentrated to give 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-5-methyl-1H-imidazole-4-carbonyl chloride.

Workup

  1. concentrationThe mixture is concentrated
  2. customto give crude 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-5-methyl-1H-imidazole-4-carboxylic acid
  3. temperaturethe resulting mixture is heated
  4. temperatureat reflux temperature for 1 hour
  5. concentrationThe mixture is concentrated

Sources & evidence

ORD record
ord-c10cccf1ccf34bc1ae216a369346c0db
Source dataset
uspto-grants-2014_05
Patent number
US08729101B2

Reaction notes

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