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

HRID 743459Notes

Reaction equation

HRID 743459 reaction equation
C[O:2][C:3](=O)[CH:4]([CH2:11][CH2:12][C:13]([CH3:16])([Cl:15])[CH3:14])[N:5]([S:7]([NH2:10])(=[O:9])=[O:8])[CH3:6].C[O-].[Na+]>CO>[CH3:14][C:13]([Cl:15])([CH3:16])[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 19424427N-(aminosulfonyl)-2-(3-methyl-3-chlorobutyl) sarcosine methyl ester

Product 1

HCID 194244574-(3-Methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(aminosulfonyl)-2-(3-methyl-3-chlorobutyl) sarcosine methyl ester (14.5 g, 50.56 mmol) in methanol (150 ml) was added to a solution of sodium methoxide (Na=2.4 g) 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- x8 H+) for 40 minutes and filtered. The filtrate was concentrated in vacuo to afford 12.54 g (97.4%) of 4-(3-methyl-3-chlorobutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1 -dioxide (Formula IV: R1 =H; R2 =(CH2)2C(Cl) (CH3)2 ; R3 =CH3) as a solid.

Workup

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

Sources & evidence

ORD record
ord-57343cb4e02f41f3aa834c2f850c4fbe
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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