Acetic Acid → HCID 14257101, Verbindung

HRID 622114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 622114
[C:1]([CH:6]=[CH:7][C:8]1[N:12]([CH3:13])[C:11]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[N:10][C:9]=1[CH3:24])([O:3][CH2:4][CH3:5])=[O:2].N(C([O-])=O)=NC([O-])=O.[K+].[K+].C(O)(=O)C>CO>[C:1]([CH2:6][CH2:7][C:8]1[N:12]([CH3:13])[C:11]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[N:10][C:9]=1[CH3:24])([O:3][CH2:4][CH3:5])=[O:2]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 6096233Potassium diazene-1,2-dicarboxylateHCID 54335975HCID 54335975, Verbindung

Produkt 1

HCID 14257101HCID 14257101, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 5-[2-(carbethoxy)ethenyl]-1,4-dimethyl-2-(4-methoxybenzylthio)imidazole (600 mg, 1.7 mmole) and potassium azodicarboxylate (29 g, 0.17 mole) in methanol (50 ml) was stirred and treated with acetic acid (7 g, 0.12 mole). The mixture was concentrated in vacuo, partitioned between methylene chloride and 5% aqueous sodium carbonate, and the organic phase was concentrated in vacuo. The residue was chromatographed on silica gel eluted with ethyl acetate to give 5-[2-(carbethoxy)ethyl]-1,4-dimethyl-2-(4-methoxybenzylthio)imidazole (mp 63° C.).

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between methylene chloride and 5% aqueous sodium carbonate
  3. concentrationthe organic phase was concentrated in vacuo
  4. customThe residue was chromatographed on silica gel
  5. washeluted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3e6e8d5b7af64071b1bcfc2688ee6149
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04769386

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