Methanol → HCID 178418812, compound

HRID 1844566Notes

Reaction equation

HRID 1844566 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.[CH3:15]O>>[NH:2]1[CH:6]=[C:5]([CH2:7][C:8]([O:10][CH3:15])=[O:9])[N:4]=[CH:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178479752HCID 178479752, compound

Product 1

HCID 178418812HCID 178418812, compound

Procedure

1H-Imidazol-4-ylacetic acid hydrochloride (20.0 g) was suspended in methanol (200 mL). To this suspension, thionyl chloride (8.87 mL) was added at room temperature, and the mixture was heated to reflux for 3 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure. To this reaction solution, a saturated aqueous solution of sodium bicarbonate was added, and the solvent was distilled off under reduced pressure. To the obtained residue, tetrahydrofuran and anhydrous magnesium sulfate were added, and insoluble matter was filtered off. The solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (14.3 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionTo this reaction solution, a saturated aqueous solution of sodium bicarbonate was added
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionTo the obtained residue, tetrahydrofuran and anhydrous magnesium sulfate were added
  7. filtrationinsoluble matter was filtered off
  8. distillationThe solvent in the filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8ceb4f70b1d94a998eb70a8f847b722b
Source dataset
uspto-grants-2015_02
Patent number
US08946443B2

Reaction notes

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