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

HRID 637031노트

반응식

HRID 637031 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3c403d0986364b28be28db4c87999d49
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194406B1

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