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

HRID 1736317Notes

Reaction equation

HRID 1736317 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 72,947.797%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-(aminosulfonyl)aminopentanoic acid methyl ester (10.5 g; 0.05 mmol) in methanol (100 ml) was added to a solution of sodium methoxide (3.78 g, from 1.61 g of Na) in 100 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 6.5 g (73%) of 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-ca1d26042d384fa299724bd22ef4c054
Source dataset
uspto-grants-1996_07
Patent number
US05541168

Reaction notes

Loading…