Ethanol → HCID 178470744, compound

HRID 1844563Notes

Reaction equation

HRID 1844563 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[N:4]=[CH:3]1.S(Cl)(Cl)=O.[CH2:15](O)[CH3:16]>>[NH:2]1[CH:6]=[C:5]([CH2:7][C:8]([O:10][CH2:15][CH3:16])=[O:9])[N:4]=[CH:3]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 178479752HCID 178479752, compound

Product 1

HCID 178470744HCID 178470744, compound

Procedure

1H-Imidazol-4-ylacetic acid hydrochloride (5.00 g) was dissolved in ethanol (100 mL). To the solution, thionyl chloride (2.46 mL) was added at room temperature, and the mixture was then heated to reflux for 3.5 hours. The reaction solvent was distilled off under reduced pressure. To the residue, a saturated aqueous solution of sodium bicarbonate was then added, and organic matter was extracted five times with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off under reduced pressure to obtain a crude product of ethyl 1H-imidazol-4-ylacetate (4.10 g).

Workup

  1. temperaturethe mixture was then heated
  2. temperatureto reflux for 3.5 hours
  3. distillationThe reaction solvent was distilled off under reduced pressure
  4. additionTo the residue, a saturated aqueous solution of sodium bicarbonate was then added
  5. extractionorganic matter was extracted five times with methylene chloride
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8c3a55b1543f4c83aa06be8792049ec4
Source dataset
uspto-grants-2015_02
Patent number
US08946443B2

Reaction notes

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