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

HRID 1392329

Reaktionsgleichung

Reaktionsgleichung von HRID 1392329
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-56be878b36844871ab083edfb91f937a
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342037B2

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