ethyl 2-((N-methylsulfamoyl)amino)acetate → 2-Methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 1392329Notes

Reaction equation

HRID 1392329 reaction equation
[CH3:1][NH:2][S:3]([NH:6][CH2:7][C:8]([O:10]CC)=O)(=[O:5])=[O:4].O(C(C)(C)C)[K]>CN(C=O)C>[CH3:1][N:2]1[C:8](=[O:10])[CH2:7][NH:6][S:3]1(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 18449915ethyl 2-((N-methylsulfamoyl)amino)acetateHCID 178418922HCID 178418922, compound

Product 1

HCID 3640772-Methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 2-((N-methylsulfamoyl)amino)acetate from the previous step (3.5 mmol) in DMF (50 mL) is added KO-t-Bu (1.56 g, 13.88 mmol) in portions under N2 at RT. The mixture is stirred overnight then quenched with HCl methanol (2 M). After the solvent is removed in vacuo, the residue is washed with water to afford 2-methyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-3-one (480 mg, 54%). 1H-NMR(CDCl3): δ 7.36 (d, J=8.4 Hz, 2H), 6.87 (d, J=8.8 Hz, 2H), 4.87 (m, 1H), 4.68 (s, 2H), 4.03 (d, J=7.2 Hz, 2H), 3.80 (s, 3H).

Workup

  1. customthen quenched with HCl methanol (2 M)
  2. customAfter the solvent is removed in vacuo
  3. washthe residue is washed with water

Sources & evidence

ORD record
ord-56be878b36844871ab083edfb91f937a
Source dataset
uspto-grants-2008_03
Patent number
US07342037B2

Reaction notes

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