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

HRID 2396781Notes

Reaction equation

HRID 2396781 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-dioxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-(aminosulfonylamino)pentanoic acid methyl ester (24.6 g; 0.117 retool) in methanol (150 ml) was added to a solution of sodium methoxide (8.86 g, from 3.77 g of Na) 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 4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =H; R2 =propyl; 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-feec91a4e05c4e7fa2d067ec6c2c8430
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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