Bis-(1H-imidazol-2-YL)-methanone → [2-(1,1,4-Trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acetic acid methyl ester

HRID 1592022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1592022
C(C1NC=CN=1)(C1NC=CN=1)=O.[S:13]([N:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH2:18][C:19](O)=[O:20])(=[O:16])(=[O:15])[NH2:14]>C1COCC1>[CH3:32][O:31][C:29](=[O:30])[CH2:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[N:17]1[CH2:18][C:19](=[O:20])[NH:14][S:13]1(=[O:16])=[O:15]

Komponenten

4

Edukt 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 67138346N-sulfamoyl-N-[2-(methoxycarbonylmethyl)-phenyl]glycine

Produkt 1

HCID 58997412[2-(1,1,4-Trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Carbonyl diimidazole (60 mg, 0.37 mmol) is added as solid to a solution of the title E compound, N-sulfamoyl-N-[2-(methoxycarbonylmethyl)-phenyl] glycine (112 mg, 0.37 mmol) in THF (5 mL). After 65 h, the solvent is removed by evaporation. The residue is taken up in EtOAc and washed with 1N aqueous HCl followed by brine. The organic solution is dried over anhydrous MgSO4, filtered and concentrated. This residue is then evaporated from diethyl ether to yield [2-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acetic acid methyl ester as a white foam: [M−1]−=283.

Aufarbeitung

  1. customthe solvent is removed by evaporation
  2. washwashed with 1N aqueous HCl
  3. dry with materialThe organic solution is dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThis residue is then evaporated from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0d62f7a2eba9495c8be49064685c6085
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291635B2

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