Thionyl Chloride → Ethyl 2-methyl-5-(2-phenylethyl)-1,3-oxazole-4-carboxylate

HRID 441714Notes

Reaction equation

HRID 441714 reaction equation
[C:1]([NH:4][CH:5]([C:11](=[O:20])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)[CH3:2].S(Cl)(Cl)=O>C(Cl)Cl>[CH3:2][C:1]1[O:20][C:11]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21417731HCID 21417731, compound

Product 1

HCID 21417734Ethyl 2-methyl-5-(2-phenylethyl)-1,3-oxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the entire oily residue obtained in Step A is added at 0° C., 60 ml. of thionyl chloride and the resulting mixture refluxed for 40 minutes. The reaction mixture is then cooled and evaporated (under vacuum) to obtain a residue. The residue is dissolved in methylene chloride, and the solution washed with 5% aqueous sodium bicarbonate (100 ml.). The organic layer is then dried over anhydrous sodium sulfate and evaporated (under vacuum) to obtain the title compound as a crude residue.

Workup

  1. temperatureThe reaction mixture is then cooled
  2. customevaporated (under vacuum)
  3. customto obtain a residue
  4. washthe solution washed with 5% aqueous sodium bicarbonate (100 ml.)
  5. dry with materialThe organic layer is then dried over anhydrous sodium sulfate
  6. customevaporated (under vacuum)

Sources & evidence

ORD record
ord-babd5c12c6cb4fdbb5ec5fcfdfdfe03c
Source dataset
uspto-grants-1977_08
Patent number
US04042596

Reaction notes

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