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

HRID 743450Notes

Reaction equation

HRID 743450 reaction equation
C[O:2][C:3](=O)[C:4]([CH2:11][CH2:12][CH3:13])(C)[NH:5][S:6]([NH2:9])(=[O:8])=[O:7].[CH3:15][O-].[Na+]>CO>[CH2:11]([CH:4]1[N:5]([CH3:15])[S:6](=[O:8])(=[O:7])[NH:9][C:3]1=[O:2])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 19424444N-aminosulfonyl-2-propyl-DL-alanine methyl ester

Product 1

HCID 189222534-Propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 125.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(aminosulfonyl)-2-propyl-DL-alanine methyl ester (10.66 g; 47.53 mmol) in methanol (100 ml) was added in one portion to a solution of sodium methoxide (prepared from 2.0 g of Na in 100 ml of dry methanol under nitrogen) and the resulting reaction mixture was stirred for 15 hours. The mixture was neutralized with BIO-RAD® 50W-X8 H+ ion exchange resin with stirring (20 minutes), and filtered. The filtrate was concentrated in vacuo to yield an oil which was dried in vacuo (4 hours) to afford 8.96 g (98%) of 4-methyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =propyl;R2 =CH3 ; R3 =H).

Workup

  1. customthe resulting reaction mixture
  2. stirringwith stirring (20 minutes)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto yield an oil which
  6. customwas dried in vacuo (4 hours)

Sources & evidence

ORD record
ord-e4b8a906673643eabff1ab02aa953ca0
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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