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

HRID 323182

반응식

HRID 323182 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

반응 조건

온도
-70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-403afb8cca9e4aef927dd4122a2a3c3e
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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