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

HRID 16977

Reaction equation

HRID 16977 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-7e5d55bd4e3e4c2b87d8e220dc3f446c
Source dataset
uspto-grants-2010_06
Patent number
US07737283B2

Linked notes

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