Sodium hydride → 1,4-Dimethyl-2-(4-methoxybenzylthio)-5-[2-(methylsulfinyl)-2-(methylthio)ethenyl]imidazole

HRID 622112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 622112
[CH3:1][N:2]1[C:6]([CH:7]=O)=[C:5]([CH3:9])[N:4]=[C:3]1[S:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.[H-].[Na+].C[CH:23]([S:27][CH:28](S(C)=O)C)[S:24]([CH3:26])=[O:25]>O1CCCC1>[CH3:1][N:2]1[C:6]([CH:7]=[C:23]([S:24]([CH3:26])=[O:25])[S:27][CH3:28])=[C:5]([CH3:9])[N:4]=[C:3]1[S:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 142571041,4-Dimethyl-5-formyl-2-(4-methoxybenzylthio)imidazoleHCID 54140058Methylmethylsulfinylmethyl sulfide

Produkt 1

HCID 541074581,4-Dimethyl-2-(4-methoxybenzylthio)-5-[2-(methylsulfinyl)-2-(methylthio)ethenyl]imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

1,4-Dimethyl-5-formyl-2-(4-methoxybenzylthio)imidazole (8 g, 0.03 mole) in tetrahydrofuran (30 ml) was added to a mixture prepared by adding sodium hydride (1.8 g, 38 mmoles) to a solution of methyl methylsulfinylmethylsulfide (4.7 g, 38 mmoles) in tetrahydrofuran. The mixture was stirred for 16 hours, concentrated in vacuo and the residue was partitioned between water and methylene chloride. The organic phase was dried with sodium sulfate, concentrated in vacuo and the residue chromatographed on silica gel eluted with ethyl acetate to give 1,4-dimethyl-2-(4-methoxybenzylthio)-5-[2-(methylsulfinyl)-2-(methylthio)ethenyl]imidazole.

Aufarbeitung

  1. customprepared
  2. concentrationconcentrated in vacuo
  3. customthe residue was partitioned between water and methylene chloride
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe residue chromatographed on silica gel
  7. washeluted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c436c1b997534d30b83ff7fc79da1253
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04769386

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