Water → Isopropyl alcohol isopropyl ether

HRID 4309

Reaktionsgleichung

Reaktionsgleichung von HRID 4309
Br[CH2:2][C:3]([C:5]1C=C(OC)C=CN=1)=[O:4].ClC1N[C:16]2[CH:22]=[CH:21]C=CC=2N=1.C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O>[CH3:2][CH:3]([OH:4])[CH3:5].[CH:3]([O:4][CH:22]([CH3:21])[CH3:16])([CH3:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 785722-ChlorobenzimidazoleHCID 198461142-Bromo-1-(4-methoxypyridin-2-yl)ethanone

Produkt 1

HCID 21202047Isopropyl alcohol isopropyl ether

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
2 °C

Versuchsvorschrift

2-Bromoacetyl-4-methoxypyridine (11.5 g, 0.05) and 2-chlorobenzimidazole (7.5 g, 0.05 mole) were dissolved in dimethylformamide (75 ml) and cooled to 2° C. K2CO3 (12 g, 0.08 mole) was added and the temperature rose to 9° C. as the suspension was stirred for 1/2 hour. The mixture was added to H2O (200 ml) giving a solid which was removed by filtration. The mother liquors were extracted with ethyl acetate and the solid was dissolved in the extracts. The organic solution was washed (brine) and dried (MgSO4) and purified by passage down a silica column and evaporated to dryness to give a sticky solid. Trituration with propan-2-ol/di-isopropyl ether gave 2-chloro-1-[2-(2-[4-methoxypyridyl])-2-oxoethyl]-benzimidazole (7.2 g).

Aufarbeitung

  1. customrose to 9° C. as the suspension
  2. customgiving a solid which
  3. customwas removed by filtration
  4. extractionThe mother liquors were extracted with ethyl acetate
  5. dissolutionthe solid was dissolved in the extracts
  6. washThe organic solution was washed (brine)
  7. dry with materialdried (MgSO4)
  8. custompurified by passage down a silica column
  9. customevaporated to dryness
  10. customto give a sticky solid

Quellen und Nachweise

ORD-Eintrag
ord-e54381d6a37d4ac89c8f8f5dc9dbc8ea
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725605

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