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

HRID 1249550Notes

Reaction equation

HRID 1249550 reaction equation
[CH3:1][CH:2]([C:4]1[N:5]=[CH:6][NH:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][CH:10]=1)[CH3:3].ClC(Cl)C(O)=O.[CH:23]([O:25][CH2:26][CH3:27])=[CH2:24].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:3][CH:2]([C:4]1[N:5]=[CH:6][N:7]([CH:23]([O:25][CH2:26][CH3:27])[CH3:24])[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][CH:10]=1)[CH3:1]

Participants

6

Reactant 4

HCID 6597Dichloroacetic AcidHCID 8023Ethyl vinyl etherHCID 14798Sodium HydroxideHCID 178503128HCID 178503128, compound

Product 1

HCID 137544744-(1-Methylethyl)-5-(4-methylthiophenyl)-1-(alpha-ethoxyethyl)imidazoleYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7.48 g (32.2 mmoles) of 4-(1-methylethyl)-5-(4-methythiophenyl)-1H-imidazole, 4.56 g (35.3 mmoles) of dichloroacetic acid and 17.57 g (0.24 mole) of ethyl vinyl ether in 350 ml of toluene were heated at reflux for 3.5 hours. The reaction mixture was cooled to room temperature and was then stirred overnight with 100 ml of 25% aqueous sodium hydroxide. The organic layer was separated and the aqueous was extracted with ether (2×). The organic fractions were combined, washed with brine, and dried over anhydrous potassium carbonate. Removal of the solvent in vacuo afforded 9.8 g of an orange oil which was used in the subsequent reaction without purification.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 3.5 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous was extracted with ether (2×)
  5. washwashed with brine
  6. dry with materialdried over anhydrous potassium carbonate
  7. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-c7b4b79a3bfb4e04b16ea4f824c28fb4
Source dataset
uspto-grants-1986_12
Patent number
US04632930

Reaction notes

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