Potassium Iodide → 1-(2,2-dimethoxyethyl)-1H-imidazole-2-carbaldehyde

HRID 1855252

Reaktionsgleichung

Reaktionsgleichung von HRID 1855252
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].Br[CH2:9][CH:10]([O:13][CH3:14])[O:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH3:12][O:11][CH:10]([O:13][CH3:14])[CH2:9][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 249551H-imidazole-2-carbaldehydeHCID 816722-Bromo-1,1-dimethoxyethane

Produkt 1

HCID 282844581-(2,2-dimethoxyethyl)-1H-imidazole-2-carbaldehydeAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of the imidazole-2-carboxaldeyde (0.41 g, 4.27 mmol) in DMF (1 mL) was added 1.1 eq. of 2-bromo-1,1-dimethoxyethane (0.79 g, 4.69 mmol), potassium carbonate and a catalytic amount of potassium iodide. The reactions were heated at 110° C. for 18 hrs followed by evaporation to dryness and purified utilizing a Biotage SP4 with a gradient method of 5-50% methanol in DCM to yield the desired compound (248 mg, 1.35 mmol, 32% yield). 1H NMR (400 MHz, DMSO-d6) δ 9.9 (s, H), 7.85 (s, H), 7.55 (s, H), 5.82 (m, H), 4.75 (d, 2H), 3.45 (s, 6H).

Aufarbeitung

  1. customfollowed by evaporation to dryness
  2. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-d7b27cecbc9d4fd2995541864e725e10
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962799B2

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