Dichloroacetic Acid → HCID 20223464, compound

HRID 1249555Notes

Reaction equation

HRID 1249555 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][CH:12]=[CH:11][CH:10]=1)[CH3:3].ClC(Cl)C(O)=O.[CH:21]([O:23][CH2:24][CH3:25])=[CH2:22].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:3][CH:2]([C:4]1[N:5]=[CH:6][N:7]([CH:21]([O:23][CH2:24][CH3:25])[CH3:22])[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:1]

Participants

6

Reactant 4

HCID 6597Dichloroacetic AcidHCID 8023Ethyl vinyl etherHCID 14798Sodium HydroxideHCID 178440195HCID 178440195, compound

Product 1

HCID 20223464HCID 20223464, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 10.0 g (0.055 mole) of 4-(1-methylethyl)-5-phenyl-1H-imidazole, 7.61 g (0.06 mole) of dichloroacetic acid and 29.3 g (0.41 mole) of ethyl vinyl ether in 585 ml of toluene was heated at reflux for 3.5 hours. The reaction mixture was cooled to room temperature and was then stirred overnight with 170 ml of 25% aqueous sodium hydroxide. The organic layer was separated. 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 under vacuum afforded 13.8 g of an oil, which was used in the subsequent reaction without purification.

Workup

  1. temperaturewas 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 under vacuum

Sources & evidence

ORD record
ord-f1f5d2b7eb3c4baeaa0fc80ac26e82f7
Source dataset
uspto-grants-1986_12
Patent number
US04632930

Reaction notes

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