HCID 131722520, compound → 5-[2-(3-Chlorophenyl)ethyl]-2-methyloxazole-4-carboxylic acid, ethyl ester

HRID 324444Notes

Reaction equation

HRID 324444 reaction equation
[C:1]([NH:4][CH:5]([C:11](=[O:21])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)[CH3:2]>S(Cl)(Cl)=O>[Cl:20][C:16]1[CH:15]=[C:14]([CH2:13][CH2:12][C:11]2[O:21][C:1]([CH3:2])=[N:4][C:5]=2[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 131722520HCID 131722520, compound

Product 1

HCID 1317225215-[2-(3-Chlorophenyl)ethyl]-2-methyloxazole-4-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

Thionyl chloride (180 ml) was added to the product of step (iii) (45.5 g) at 0° C. The mixture was stirred at room temperature for 2 hours and heated at reflux for 40 min. The residue after evaporation under reduced pressure was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase was dried (MgSO4) and solvent evaporated under reduced pressure. Purification was by chromatography eluting with 1-2% ethanol in dichloromethane to give the subtitle product as an orange oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 40 min
  3. customThe residue after evaporation under reduced pressure
  4. dissolutionwas dissolved in ethyl acetate
  5. washwashed with saturated sodium bicarbonate solution
  6. dry with materialThe organic phase was dried (MgSO4) and solvent
  7. customevaporated under reduced pressure
  8. customPurification
  9. washeluting with 1-2% ethanol in dichloromethane

Sources & evidence

ORD record
ord-808755a7ac7948b393fbc4954dd8baaa
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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