Ethyl Thioglycolate → HCID 86742259, compound

HRID 845048Notes

Reaction equation

HRID 845048 reaction equation
[N+:1]([C:4]1[C:5](Cl)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[SH:11][CH2:12][C:13]([O:15]CC)=[O:14].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:12]([C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=1)[CH3:13].[SH:11][CH2:12][C:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 796132-Chloro-3-nitropyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 86742259HCID 86742259, compoundYield 127.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 50 g of 3-nitro-2-chloropyridine and 38 g of ethyl mercaptoacetate in 400 ml of ethanol containing 30 g of sodium bicarbonate is heated under reflux for 7 hours. The solution is subsequently concentrated in vacuo and then, after cooling, the residue is treated with water and ice and extracted with ether. The ether phase is washed with water and dried, the solvent is evaporated off and a residue is recovered which crystallizes from isopropyl ether. The crystals are filtered off and dried to give 49 g of ethyl 3-nitropyridine-2-mercaptoacetate in the form of crystals of melting point 58° C.

Workup

  1. temperatureunder reflux for 7 hours
  2. concentrationThe solution is subsequently concentrated in vacuo
  3. temperatureafter cooling
  4. additionthe residue is treated with water and ice
  5. extractionextracted with ether
  6. washThe ether phase is washed with water
  7. customdried
  8. customthe solvent is evaporated off
  9. customa residue is recovered which
  10. customcrystallizes from isopropyl ether
  11. filtrationThe crystals are filtered off
  12. customdried

Sources & evidence

ORD record
ord-ef4ec27515484feeb3cd957491d6d5a4
Source dataset
uspto-grants-1988_07
Patent number
US04755509

Reaction notes

Loading…