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

HRID 1736310Notes

Reaction equation

HRID 1736310 reaction equation
[CH3:1][O-].[Na+].C[O:5][C:6](=O)[CH:7]([CH:13]([CH3:15])C)[NH:8][S:9]([NH2:12])(=[O:11])=[O:10]>CO>[CH2:13]([CH:7]1[NH:8][S:9](=[O:11])(=[O:10])[NH:12][C:6]1=[O:5])[CH2:15][CH3:1]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 19424464N-(aminosulfonyl)-DL-valine methyl ester

Product 1

HCID 189222484-Propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 116,489.297%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of freshly prepared sodium methoxide (6.41 g, from 2.3 g of Na) in 100 ml of methanol was added a solution of N-(aminosulfonyl)-DL-valine methyl ester (16.6 g; 0.079 mmol) in methanol (150 ml) and the resulting reaction mixture was stirred for 6 hours. The mixture was cooled, neutralized with BIO-RAD® 50W-X8 H+ ion exchange resin, and filtered. The filtrate was concentrated in vacuo to afford 16.4 g of a crude 4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =H; R2 =isopropyl; R3 =H).

Workup

  1. customthe resulting reaction mixture
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d139d52351a44cab807717ecd1a869d4
Source dataset
uspto-grants-1996_07
Patent number
US05541168

Reaction notes

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