2-Chlorobenzimidazole → 1-ethoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane

HRID 637031ノート

反応式

HRID 637031 の反応式
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl[C:14]1[NH:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1>CO>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:14]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 785722-ChlorobenzimidazoleHCID 15289249Ethyl 1,4-diazepane-1-carboxylate

生成物 1

HCID 184650911-ethoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
130 °C

実験手順

Combine 1-ethoxycarbonyl[1,4]diazepane (36.6 g, 212 mmol) and 2-chlorobenzimidazole (18.0 g, 106 mmol). Heat to 130° C. After 4 hours, cool to ambient temperature and add hot methanol to dissolve the reaction mixture. Partition the methanol solution between dichloromethane (700 mL) and a solution of sodium hydroxide (20 g) in water (500 mL). Separate the layers and extract the aqueous layer three times with dichloromethane. Combine the organic layers, extract with brine, dry over Na2SO4, filter, and evaporate in vacuo to give a solid. Triturate the solid with ethyl acetate (100 mL) and cool to 0° C. Collect solid by filtration and dry in vacuo to give 1-ethoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane.

後処理

  1. temperaturecool to ambient temperature
  2. dissolutionto dissolve the reaction mixture
  3. customPartition the methanol solution between dichloromethane (700 mL)
  4. customSeparate the layers
  5. extractionextract the aqueous layer three times with dichloromethane
  6. extractionextract with brine
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a solid
  11. customTriturate the solid with ethyl acetate (100 mL)
  12. temperaturecool to 0° C
  13. customCollect solid
  14. filtrationby filtration
  15. customdry in vacuo

出典と根拠

ORDレコード
ord-3c403d0986364b28be28db4c87999d49
出典データセット
uspto-grants-2001_02
特許番号
US06194406B1

反応ノート

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