Hydrogen Peroxide → HCID 11789721, compound

HRID 374099Notes

Reaction equation

HRID 374099 reaction equation
[NH2:1][C:2]1[CH2:3][S:4][CH2:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[OH:11]O>C(O)(C)C>[NH2:1][C:2]1[CH2:3][S:4](=[O:11])[CH2:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 10898974HCID 10898974, compound

Product 1

HCID 11789721HCID 11789721, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

3.2 g (0.02 mol) of 3-amino-4-methoxycarbonyl-2,5-dihydrothiophene are suspended in 30 ml of isopropanol. 2.2 ml of 35% strength hydrogen peroxide are added, with cooling. The mixture is then stirred at an internal temperature of 50° C. until starting material can no longer be detected in a thin layer chromatogram (approx. 5 hours). The mixture is then cooled in an ice bath and the precipitated crystals are filtered off with suction and washed with ice-cold isopropanol and with diethyl ether. Yield: 3.5 g (91% of theory). When recrystallized from methanol, the crystals melt at 137°-140° C.

Workup

  1. temperaturewith cooling
  2. customcan no longer be detected in a thin layer chromatogram (approx. 5 hours)
  3. temperatureThe mixture is then cooled in an ice bath
  4. filtrationthe precipitated crystals are filtered off with suction
  5. washwashed with ice-cold isopropanol and with diethyl ether
  6. customWhen recrystallized from methanol
  7. custommelt at 137°-140° C.

Sources & evidence

ORD record
ord-bb0e2b8316a446779e9964e6fda1eb99
Source dataset
uspto-grants-1992_11
Patent number
US05166346

Reaction notes

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