Sodium Methoxide → 4-(3-Methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 1721620Notes

Reaction equation

HRID 1721620 reaction equation
C[O:2][C:3](=O)[CH:4]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[N:5]([S:7]([NH2:10])(=[O:9])=[O:8])[CH3:6].C[O-].[Na+]>CO>[CH3:14][CH:13]([CH3:15])[CH2:12][CH2:11][CH:4]1[N:5]([CH3:6])[S:7](=[O:9])(=[O:8])[NH:10][C:3]1=[O:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18922252N-(aminosulfonyl)-2-(3-methylbutyl)sarcosine methyl ester

Product 1

HCID 189222624-(3-Methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(aminosulfonyl)-2-(3-methylbutyl)-sarcosine methyl ester (12.28 g, 48.67 mmol) in methanol (150 ml) was added under nitrogen to a solution of sodium methoxide (Na=2.1 g, 95.71 mmol) in 150 ml of ice-cold methanol. The resulting reaction mixture was stirred at room temperature under nitrogen for 1.5 hours, and the mixture was treated with 25 g of ion-exchange resin (BIO RAD® 50W×8H+ ; 200-400 mesh) for 40 minutes and filtered. The filtrate was concentrated in vacuo to afford 10.7 g (99.8%) of 4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin3-one 1,1-dioxide (Formula V: R1 =H; R2 =(CH2)2CH(CH3)2 ; R3 =CH3) as a solid, m.p. 212°-214° C.

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cecb30f7caa14b0488c980a68420e304
Source dataset
uspto-grants-1996_04
Patent number
US05512576

Reaction notes

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