Hydrochloric Acid → 3-Ethoxycarbonylmethyl-2-hydrazonothiazolidin-4-one

HRID 21410Notes

Reaction equation

HRID 21410 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:11](=[O:12])[CH2:10][S:9][C:8]1=[N:13][N:14]=C(C)C)=[O:5])[CH3:2].Cl.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:11](=[O:12])[CH2:10][S:9][C:8]1=[N:13][NH2:14])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 544639313-Ethoxycarbonylmethyl-2-isopropylidenehydrazonothiazolidin-4-one

Product 1

HCID 542741023-Ethoxycarbonylmethyl-2-hydrazonothiazolidin-4-oneYield 51.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 2.0 g of 3-ethoxycarbonylmethyl-2-isopropylidenehydrazonothiazilidin-4-one obtained in step (1) of Example 9 was added 30 ml of 0.5N hydrochloric acid, and the mixture was subjected to steam distillation for 15 minutes. The reaction mixture obtained was cooled, the resulting precipitates were distilled off, and the filtrate was concentrated under reduced pressure. To the residue formed were added a saturated sodium hydrogencarbonate solution and chloroform to distribute the residue between them. The organic layer was washed three times with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue formed was charged on silica gel column chromatography and eluted with a mixture of chloroform and ethyl acetate at 4:1 by volume to obtain 870 mg of 3-ethoxycarbonylmethyl-2-hydrazonothiazolidin-4-one.

Workup

  1. distillationthe mixture was subjected to steam distillation for 15 minutes
  2. customThe reaction mixture obtained
  3. temperaturewas cooled
  4. customthe resulting precipitates
  5. distillationwere distilled off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customTo the residue formed
  8. washThe organic layer was washed three times with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue formed
  12. additionwas charged on silica gel column chromatography
  13. washeluted with a mixture of chloroform and ethyl acetate at 4:1 by volume

Sources & evidence

ORD record
ord-0c412183a26b4b4298ba27bfa81d3641
Source dataset
uspto-grants-1995_06
Patent number
US05422360

Reaction notes

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