Tetrahydrofuran → 2-chloro-1-(2-ethoxyethyl)-1H-benzimidazole

HRID 323182

Reaktionsgleichung

Reaktionsgleichung von HRID 323182
[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[O:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(OCCCl)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:12]([O:11][CH2:15][CH2:14][N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[Cl:1])[CH3:13]

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 785722-ChlorobenzimidazoleHCID 3251421Potassium bis(trimethylsilyl)amide

Produkt 1

HCID 104893562-chloro-1-(2-ethoxyethyl)-1H-benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

Combine 2-chloro-1H-benzimidazole (15.3 g, 100 mmol) and tetrahydrofuran (300 mL). Cool to −70° C. Add dropwise, a solution of potassium bis(trimethylsilyl)amide (200 mL, 0.5 M in toluene, 100 mmol). After 30 minutes, add 2-chloroethyl ethyl ether (22.2 g, 200 mmol) and tetrabutylammonium bromide (0.5 g). Warm to ambient temperature and heat to reflux. After 12 hours, cool to ambient temperature and add water. Separate the organic layer and extract the aqueous layer with dichloromethane. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give 1-(2-ethoxyethyl)-2-chloro-1H-benzimidazole.

Aufarbeitung

  1. additionAdd dropwise
  2. temperatureWarm to ambient temperature
  3. temperatureheat to reflux
  4. waitAfter 12 hours
  5. temperaturecool to ambient temperature
  6. customSeparate the organic layer
  7. extractionextract the aqueous layer with dichloromethane
  8. dry with materialDry the combined organic layers over Na2SO4
  9. filtrationfilter
  10. customevaporate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-403afb8cca9e4aef927dd4122a2a3c3e
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211199B1

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