Hydrochloric Acid → 3,3-Dimethyl-1lambda6,2-thiazolidine-1,1-dione

HRID 501245Notes

Reaction equation

HRID 501245 reaction equation
[NH2:1][C:2]([CH3:16])([CH3:15])[CH2:3][CH2:4][S:5](OC1C=CC=CC=1)(=[O:7])=[O:6].[OH-].[K+].O.Cl>C1COCC1>[CH3:15][C:2]1([CH3:16])[CH2:3][CH2:4][S:5](=[O:7])(=[O:6])[NH:1]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14797Potassium Hydroxide3×HCID 86243860Phenyl 3-amino-3-methylbutane-1-sulfonate

Product 1

HCID 596494563,3-Dimethyl-1lambda6,2-thiazolidine-1,1-dioneYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

11.58 g of phenyl 3-amino-3-methylbutane-1-sulfonate and 5.34 g of KOH were boiled under reflux in 240 ml of THF/95 ml of water for 7 hours. Then a further 2.7 g of KOH, 50 ml of water and 120 ml of THF were added, and the mixture was again boiled under reflux for 7 hour. Then a further 5.34 g of KOH were added, and the mixture was again boiled under reflux for 3 hours. It was allowed to cool and then 300 ml of a 2N aqueous HCl solution were added, and the mixture was extracted 5 times with 250 ml of EA each time. After drying over Na2SO4, the solvent was removed in vacuo. Chromatography on silica gel with EA/HEP 1:1 afforded 3.82 g of white crystals, mp 72° C.

Workup

  1. temperatureunder reflux for 7 hour
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool
  4. extractionthe mixture was extracted 5 times with 250 ml of EA each time
  5. dry with materialAfter drying over Na2SO4
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5cb75ee220954b6aaeb47e4f6ac4d92c
Source dataset
uspto-grants-2010_08
Patent number
US07772262B2

Reaction notes

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