Ethyl Thioglycolate → HCID 12038723, compound

HRID 1978353Notes

Reaction equation

HRID 1978353 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([SH:10])=[CH:8][CH:7]=[CH:6][C:5]=12.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:12]S.[O-][CH2:19]C.[Na+]>C(O)C>[N:1]1[CH:2]=[C:3]2[N:4]3[C:9](=[CH:8][CH:7]=[CH:6][C:5]=13)[S:10][C:12]([C:11]([O:15][CH2:16][CH3:17])=[O:14])=[CH:19]2

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxideHCID 178418687HCID 178418687, compound

Product 1

HCID 12038723HCID 12038723, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of imidazo[1,2-a]pyridine-5-thiol (448 mg), ethyl thioglycolate (0.36 ml), and sodium ethoxide (210 mg) in ethanol (10 ml) was refluxed with stirring for 3 hours. The mixture was then allowed to cool and concentrated. The residue was diluted with ethyl acetate (10 ml) and extracted with 1N-hydrochloric acid. The aqueous layer was neutralized with 1N-NaOH/water and extracted with ethyl acetate, and the organic layer was washed with water and concentrated. The resulting crystals were collected, rinsed with diisopropyl ether (20 ml), and dried to provide the title compound (430 mg, 65%).

Workup

  1. temperatureto cool
  2. concentrationconcentrated
  3. additionThe residue was diluted with ethyl acetate (10 ml)
  4. extractionextracted with 1N-hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washthe organic layer was washed with water
  7. concentrationconcentrated
  8. customThe resulting crystals were collected
  9. washrinsed with diisopropyl ether (20 ml)
  10. customdried

Sources & evidence

ORD record
ord-9e5e4bfc32ca4596874d20e200028fbe
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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