Sodium Methoxide → 4-Propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 1289623Notes

Reaction equation

HRID 1289623 reaction equation
C[O:2][C:3](=O)[CH:4]([NH:8][S:9]([NH2:12])(=[O:11])=[O:10])[CH2:5][CH2:6][CH3:7].C[O-].[Na+]>CO>[CH2:5]([CH:4]1[NH:8][S:9](=[O:11])(=[O:10])[NH:12][C:3]1=[O:2])[CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 539168252-(Aminosulfonylamino)pentanoic acid methyl ester

Product 1

HCID 189222484-Propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 105.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-(aminosulfonylamino)pentanoic acid methyl ester (24.6 g, 0.11 mol) in methanol (150 ml) was added to a solution of sodium methoxide (8.86 g, 0.164 mol) in 150 ml of methanol and the resulting reaction mixture was refluxed for 18 hours. The mixture was cooled, neutralized with BIO-RAD® 50W-X8 H+ ion exchange resin, and filtered. The filtrate was concentrated in vacuo to yield an oil which was crystallized from methanol/hexane to afford 20.73 g (theory) of 4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =propyl; R2 =R3 =H).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 18 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto yield an oil which
  7. customwas crystallized from methanol/hexane

Sources & evidence

ORD record
ord-86e9305e52544626a66e8f1103f9c6f2
Source dataset
uspto-grants-1998_05
Patent number
US05750546

Reaction notes

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