Sodium Hydroxide → 8-(5-Methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline

HRID 1088813ノート

反応式

HRID 1088813 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8](Cl)[NH:9][C:5]=2[CH:4]=1.NC(N)=[S:15].Cl.[CH3:18][N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[CH2:29]Cl)[CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>O.C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([S:15][CH2:29][C:27]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:28]=3[N:19]([CH3:18])[CH2:20][CH2:21][CH2:22]4)[NH:9][C:5]=2[CH:4]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 5191972-Chloro-5-methoxy-1H-benzimidazoleHCID 2723790ThioureaHCID 221617911-Methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline hydrochloride

生成物 1

HCID 150533328-(5-Methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline収率 83.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 962Water溶媒

実験手順

5-Methoxy-2-chlorobenzimidazole (0.55 g), thiourea (0.2 g) and ethanol (10 ml) were refluxed for 2 hours. To the reaction mixture was added a solution of 1-methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline hydrochloride (0.51 g) and sodium hydroxide (0.3 g) in water (5 ml) and the mixture was refluxed for 5 hours. After completion of the reaction, ethanol was distilled off and water was added to the resulting residue, and the mixture was extracted with chloroform. After drying over anhydrous magnesium sulfate, chloroform was distilled off. The resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (4:1)] to give 8-(5-methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline (0.62 g).

後処理

  1. temperaturethe mixture was refluxed for 5 hours
  2. distillationwas distilled off
  3. additionwater was added to the resulting residue
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialAfter drying over anhydrous magnesium sulfate, chloroform
  6. distillationwas distilled off
  7. customThe resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (4:1)]

出典と根拠

ORDレコード
ord-df696adb185e4742983da6ba8101c272
出典データセット
uspto-grants-1990_10
特許番号
US04963566

反応ノート

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