Sodium hydride → 2,4,5,6,7-Pentachloro-1-(2-acetoxyethoxymethyl)benzimidazole

HRID 2379067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2379067
[H-].[Na+].[Cl:3][C:4]1[NH:5][C:6]2[C:12]([Cl:13])=[C:11]([Cl:14])[C:10]([Cl:15])=[C:9]([Cl:16])[C:7]=2[N:8]=1.[C:17]([O:20][CH2:21][CH2:22][O:23][CH2:24]Br)(=[O:19])[CH3:18]>CC#N>[Cl:3][C:4]1[N:5]([CH2:24][O:23][CH2:22][CH2:21][O:20][C:17](=[O:19])[CH3:18])[C:6]2[C:12]([Cl:13])=[C:11]([Cl:14])[C:10]([Cl:15])=[C:9]([Cl:16])[C:7]=2[N:8]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 3676562-(Bromomethoxy)ethyl acetateHCID 232739742,4,5,6,7-pentachloro-1H-benzimidazole

Produkt 1

HCID 186975732,4,5,6,7-Pentachloro-1-(2-acetoxyethoxymethyl)benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

NaH (0.12 g, 3.0 mmole, 60% oil disperson) was added to a stirred suspension of 2,4,5,6,7-pentachlorobenzimidazole (14) (1.0 g, 3.4 mmole) in dry CH3CN (120 mL) under a N2 atmosphere. The solution was stirred until H2 evolution has ceased and a clear solution was obtained (20 min.). (2-Acetoxyethoxy) methyl bromide (0.68 g, 10.66 mmole) in CH3CN (34 mL) was then added dropwise. The reaction mixture was stirred for an additional 3 hr. The resulting mixture was concentrated under reduced pressure, diluted with H2O (50 mL), extracted with EtOAc (100 mL), washed with H2O (100 mL), dried (anhyd. Na2SO4) and the solvent was removed under reduced pressure to yield an oil (165). The resulting oil was purified by flash column chromatography (2×24 cm) (230-400 mesh). Elution of the column with hexane:EtOAc (6:4, v/v) and evaporation of the appropriate fractions gave a solid which was recrystallized from MeOH to afford 1.39 g (72%) of 165: m.p. 119° C. 1H NMR (CDCl3): d 5.93 (s, 2, H, C-1'), 4.143.92 (m, 4, H, C-3' and C-4'), 1.83 (s, 3 H, Ac). Anal. Calcd. for C12H9N2Cl5O3 : C,35.45; H, 2.23; N, 6.89. Found: C,35.57; H, 2.17; N, 16.91.

Aufarbeitung

  1. customa clear solution was obtained (20 min.)
  2. stirringThe reaction mixture was stirred for an additional 3 hr
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. additiondiluted with H2O (50 mL)
  5. extractionextracted with EtOAc (100 mL)
  6. washwashed with H2O (100 mL)
  7. dry with materialdried (anhyd. Na2SO4)
  8. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dd1825c301ad42ddadfe48af9e09e6c9
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05360795

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