Ethanol → HCID 178440079, compound

HRID 1918238Notes

Reaction equation

HRID 1918238 reaction equation
[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:13][CH2:14][CH3:15])[NH:8][C:9]=1[C:10]([OH:12])=[O:11])([CH3:4])[CH3:3].S(Cl)(Cl)=O.[CH2:20](O)[CH3:21]>>[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:13][CH2:14][CH3:15])[NH:8][C:9]=1[C:10]([O:12][CH2:20][CH3:21])=[O:11])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 178440085HCID 178440085, compound2×

Product 1

HCID 178440079HCID 178440079, compoundYield 85%

Procedure

3.0 grams of 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid (formula III) from Example 4, 30 ml of ethanol, and 3.36 grams of thionyl chloride were added into 100 ml three-necked flask, and refluxed until the reaction completed. The reaction mixture was then allowed to cool to ambient temperature, the solvent was evaporated, 30 ml of ethyl acetate and 30 ml of water were added, and the mixture was adjusted to basic using sodium bicarbonate. The organic layer was separated and the aqueous layer was further extracted with 10 ml×3 of ethyl acetate. The organic portion was washed once with saturated saline solution, dried over anhydrous magnesium sulfate and filtered, the solvent was evaporated to give 2.9 grams of ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate, resulting in a yield of 85%.

Workup

  1. temperaturerefluxed until the reaction
  2. customthe solvent was evaporated
  3. addition30 ml of ethyl acetate and 30 ml of water were added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was further extracted with 10 ml×3 of ethyl acetate
  6. washThe organic portion was washed once with saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7ed22cdad6e847f2b071403a20044737
Source dataset
uspto-grants-2013_12
Patent number
US08618308B2

Reaction notes

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