Dichloroacetic Acid → 4-Phenyl-5-(4-methylthiophenyl)-1-(alpha-ethoxyethyl)imidazole

HRID 482913Notes

Reaction equation

HRID 482913 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(Cl)C(O)=O.[CH:26]([O:28][CH2:29][CH3:30])=[CH2:27].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]1([C:7]2[N:8]=[CH:9][N:10]([CH:26]([O:28][CH2:29][CH3:30])[CH3:27])[C:11]=2[C:12]2[CH:13]=[CH:14][C:15]([S:18][CH3:19])=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6597Dichloroacetic AcidHCID 8023Ethyl vinyl etherHCID 14798Sodium HydroxideHCID 13580029HCID 13580029, compound

Product 1

HCID 543654074-Phenyl-5-(4-methylthiophenyl)-1-(alpha-ethoxyethyl)imidazoleYield 100.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 12.0 g (0.045 mole) of 4-phenyl-5-(4-methylthiophenyl)-1H-imidazole, 6.7 g (0.052 mole) of dichloroacetic acid and 24.6 g (0.34 mole) of ethyl vinyl ether in 485 ml of toluene was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature and was then stirred overnight with 130 ml of 25% aqueous sodium hydroxide. The organic layer was separated and the aqueous layer was extracted with ether (2X). The organic fractions were combined, washed with brine and dried over anhydrous potassium carbonate. Removal of the solvent under vacuum afforded 15.3 g of an oil. The product was used in the subsequent reaction without purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ether (2X)
  5. washwashed with brine
  6. dry with materialdried over anhydrous potassium carbonate
  7. customRemoval of the solvent under vacuum

Sources & evidence

ORD record
ord-611f79cd7c734988abfd65086f21e7d5
Source dataset
uspto-grants-1986_03
Patent number
US04576958

Reaction notes

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