1-Butanol → 5,5-Dimethyl-1,3-thiazolidine-2,4-dione

HRID 1093990Notes

Reaction equation

HRID 1093990 reaction equation
Br[C:2]([CH3:8])([CH3:7])[C:3](OC)=[O:4].[NH2:9][C:10](N)=[S:11].C([OH:17])CCC>>[CH3:8][C:2]1([CH3:7])[S:11][C:10](=[O:17])[NH:9][C:3]1=[O:4]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 90097Methyl 2-bromo-2-methylpropionateHCID 2723790Thiourea

Product 1

HCID 133258305,5-Dimethyl-1,3-thiazolidine-2,4-dione

Conditions

Temperature
110 °C

Procedure

41.4 mmoles of methyl 2-bromo-2-methyl-propionate and 4.56 mmoles of thiourea are dissolved in n-butanol (90 mL) and stirred at 110° C. for 5 hours. The solvent is evaporated to dryness and the residue is taken up in ethanol (120 ml) and HCl (2N, 120 mL) and then heated at reflux for 16 hours. The ethanol is evaporated off and the mixture is diluted with water (120 ml) and then extracted with AcOEt. The organic phase is washed with saturated NaCl solution, dried over magnesium sulphate, filtered and evaporated to dryness. The crystals obtained are washed with pentane, filtered off and dried in vacuo to yield the title product.

Workup

  1. customThe solvent is evaporated to dryness
  2. temperatureHCl (2N, 120 mL) and then heated
  3. temperatureat reflux for 16 hours
  4. customThe ethanol is evaporated off
  5. additionthe mixture is diluted with water (120 ml)
  6. extractionextracted with AcOEt
  7. washThe organic phase is washed with saturated NaCl solution
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe crystals obtained
  12. washare washed with pentane
  13. filtrationfiltered off
  14. customdried in vacuo

Sources & evidence

ORD record
ord-4729a8006ca3467b86d97072d8b38df1
Source dataset
uspto-grants-2012_03
Patent number
US08133889B2

Reaction notes

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