Methanol → HCID 68710823, compound

HRID 2097554Notes

Reaction equation

HRID 2097554 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].S(Cl)(Cl)=O.[CH3:27]O>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([CH2:18][CH2:19][C:20]([O:22][CH3:27])=[O:21])[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 68704548HCID 68704548, compound

Product 1

HCID 68710823HCID 68710823, compoundYield 68%

Procedure

A solution (2.3 l) of 3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]propionic acid (254.5 g) in methanol was ice-cooled, and 58 ml of thionyl chloride was added dropwise. After completion of the addition, the resulting mixture was heated under reflux for 2 hours and cooled to room temperature. The solvent was distilled off under reduced pressure, and the residue was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3). The solvent was distilled off under reduced pressure, and the residue was recrystallized from an ethyl acetate/n-hexane mixed solvent, to thereby obtain 219.35 g (yield: 68%) of methyl 3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]propionate as a white powder.

Workup

  1. temperaturecooled
  2. additionAfter completion of the addition
  3. temperaturethe resulting mixture was heated
  4. temperatureunder reflux for 2 hours
  5. distillationThe solvent was distilled off under reduced pressure
  6. extractionthe residue was subjected to extraction with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3)
  11. distillationThe solvent was distilled off under reduced pressure
  12. customthe residue was recrystallized from an ethyl acetate/n-hexane mixed solvent

Sources & evidence

ORD record
ord-07df89a68aec421a9392f623262f3c9c
Source dataset
uspto-grants-2013_05
Patent number
US08450352B2

Reaction notes

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