Ethanol → 7-Chloro-3-(1-imidazolylmethyl)-2-methylimidazo[2,1-a]isoquinoline

HRID 649152노트

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HRID 649152 반응식
C(O)C.COS([O-])(=O)=O.[Cl:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][N:15]1[C:23]([CH2:24][N+](C)(C)C)=[C:22]([CH3:29])[N:21]=[C:16]12.[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1>CS(C)=O>[Cl:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][N:15]1[C:23]([CH2:24][C:31]3[NH:30][CH:34]=[CH:33][N:32]=3)=[C:22]([CH3:29])[N:21]=[C:16]12

참가 물질

5

반응물 3

HCID 702EthanolHCID 795ImidazoleHCID 138218647-Chloro-2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline methylsulfate

생성물 1

HCID 704198067-Chloro-3-(1-imidazolylmethyl)-2-methylimidazo[2,1-a]isoquinoline수율 41%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
100 °C

실험 절차

Ethanol (50 ml) was added to a mixture of 7-chloro-2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline methylsulfate (2.3 g) and imidazole (0.95 g) in dimethyl sulfoxide (20 ml) and heated at 100° C. with stirring for 5 hours. After the removal of ethanol by distillation, the residue was poured into water. The resulting precipitates were collected by filtration, dried and recrystallized from ethyl acetate. The obtained crystals were chromatographed on silica gel (16 g) with a mixture of chloroform and methanol (10:1) as an eluent. The eluates were evaporated in vacuo and the residual solid was recrystallized from ethyl acetate to give 7-chloro-3-(1-imidazolylmethyl)-2-methylimidazo[2,1-a]isoquinoline (0.7 g).

후처리

  1. customAfter the removal of ethanol
  2. distillationby distillation
  3. additionthe residue was poured into water
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. customdried
  7. customrecrystallized from ethyl acetate
  8. customThe obtained crystals were chromatographed on silica gel (16 g) with a mixture of chloroform and methanol (10:1) as an eluent
  9. customThe eluates were evaporated in vacuo
  10. customthe residual solid was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-d3fcd37c1fb04a1a9f81100b2f53b7e0
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04738967

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