Potassium Iodide → Ethyl 4-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridinecarboxylate

HRID 1828427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1828427
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=1.Cl[CH2:14][C:15]1[S:16][CH:17]=[C:18]([CH:20]([CH3:22])[CH3:21])[N:19]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:20]([C:18]1[N:19]=[C:15]([CH2:14][O:1][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=2)[S:16][CH:17]=1)([CH3:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 220637012-(Chloromethyl)-4-isopropylthiazoleHCID 178469317HCID 178469317, Verbindung

Produkt 1

HCID 22063568Ethyl 4-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridinecarboxylateAusbeute 46,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Ethyl 4-hydroxy-2-pyridinecarboxylate (19.5 g, 0.057 mol) dissolved in dimethylformamide (200 ml) was added with a solution of 2-(chloromethyl)-4-isopropyl-1,3-thiazole (11 g, 0.063 mol) in dimethylformamide (150 ml). The mixture was added with potassium iodide (9.5 g) and potassium carbonate (12 g) at room temperature, then heated to 110° C. and stirred for 1 hour. The reaction solution was returned to room temperature, and the solvent was evaporated under reduced pressure. The residue was diluted with chloroform and washed with water. The resulting organic layer was washed with saturated brine, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (chloroform) to obtain 8.049 g (46%) of the title compound.

Aufarbeitung

  1. customwas returned to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was diluted with chloroform
  4. washwashed with water
  5. washThe resulting organic layer was washed with saturated brine
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-1abc6c72148649ca874c2d0ccc4b616f
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07056917B2

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