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

HRID 2396772Notes

Reaction equation

HRID 2396772 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 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2- (aminosulfonyl) aminopentanoic acid methyl ester (13 g; 0.05 retool) in methanol (150 ml) was added to a solution of sodium methoxide (5.54 g, from 2 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 10.8 g (quantitative) 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-9750c736c81140dfb03ae6725f1fed69
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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