Imidazole → 2-(1-Imidazolyl)-1-phosphonoethanesulfonic acid

HRID 2691

Reaktionsgleichung

Reaktionsgleichung von HRID 2691
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C[O:7][P:8]([O:17]C)([C:10]([S:12]([O:15]C)(=[O:14])=[O:13])=[CH2:11])=[O:9].Br[Si](C)(C)C.O>C(Cl)(Cl)Cl>[N:1]1([CH2:11][CH:10]([P:8]([OH:17])([OH:9])=[O:7])[S:12]([OH:15])(=[O:14])=[O:13])[CH:5]=[CH:4][N:3]=[CH:2]1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 76113BromotrimethylsilaneHCID 18936079Methyl 1-dimethoxyphosphinylethenesulfonate

Produkt 1

HCID 189360762-(1-Imidazolyl)-1-phosphonoethanesulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 0.68 g (0.01 mole) of imidazole and 2.30 g (0.01 mole) of methyl 1-dimethoxyphosphinylethenesulfonate (U.S. Pat. No. 5,011,938 issued to Barnett et al. on Apr. 30, 1991) in 20 ml of chloroform is stirred at 20°-50° for one day. The reaction is cooled to room temperature, and 10.7 g (0.07 mole) of bromotrimethylsilane is added. The mixture is stirred at 20°-30° for 2-3 days, and to it is then added 20 ml water. The mixture is stirred for about 30 minutes, and the layers are separated. The water layer is extracted several times with CHCl3 (extracts are discarded) and is evaporated to dryness under vacuum. The residue is triturated with acetone to give a solid, which is collected by filtration and recrystallized from water/acetone to afford 2-(1-imidazolyl)-1-phosphonoethanesulfonic acid.

Aufarbeitung

  1. stirringThe mixture is stirred for about 30 minutes
  2. customthe layers are separated
  3. extractionThe water layer is extracted several times with CHCl3 (extracts are discarded)
  4. customis evaporated to dryness under vacuum
  5. customThe residue is triturated with acetone
  6. customto give a solid, which
  7. filtrationis collected by filtration
  8. customrecrystallized from water/acetone

Quellen und Nachweise

ORD-Eintrag
ord-b61bb71ca3fc444f88d24d728812b5de
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731299

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