ethyl 2-((N-(p-methoxybenzyl)sulfamoyl)amino)acetate → 2-(4-Methoxybenzyl)-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 16969

Reaktionsgleichung

Reaktionsgleichung von HRID 16969
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][NH:8][S:9]([NH:12][CH2:13][C:14](OCC)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.O(C(C)(C)C)[K]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:14](=[O:15])[CH2:13][NH:12][S:9]2(=[O:11])=[O:10])=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 18449916ethyl 2-((N-(p-methoxybenzyl)sulfamoyl)amino)acetateHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 588428642-(4-Methoxybenzyl)-1,2,5-thiadiazolidin-3-one 1,1-dioxideAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-((N-(p-methoxybenzyl)sulfamoyl)amino)acetate from the previous step (1.0 g, 3.47 mmol) in DMF (50 mL) was added KO-t-Bu (1.56 g, 13.88 mmol) in portions under N2 atmosphere at RT. The mixture was stirred overnight then quenched with HCl/methanol (2 M). After the solvent was removed in vacuo, the residue was washed with water to afford 2-(4-methoxy-benzyl)-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 was removed in vacuo
  3. washthe residue was washed with water

Quellen und Nachweise

ORD-Eintrag
ord-bf3a4e0577384e76a1c67d7e38daef07
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737283B2

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