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

HRID 649152ノート

反応式

HRID 649152 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d3fcd37c1fb04a1a9f81100b2f53b7e0
出典データセット
uspto-grants-1988_04
特許番号
US04738967

反応ノート

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