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

HRID 323182

反応式

HRID 323182 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒

反応条件

温度
-70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-403afb8cca9e4aef927dd4122a2a3c3e
出典データセット
uspto-grants-2001_04
特許番号
US06211199B1

関連ノート

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