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

HRID 1088814ノート

反応式

HRID 1088814 の反応式
Cl.[C:2]([S:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]([CH3:17])[CH2:14][CH2:13][CH2:12]2)(O)=O.[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([NH2:27])=[C:24]([NH2:26])[CH:25]=1.N>Cl>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]2[N:27]=[C:2]([S:5][CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:16]=3[N:15]([CH3:17])[CH2:14][CH2:13][CH2:12]4)[NH:26][C:24]=2[CH:25]=1

参加物

5

反応物 3

HCID 222AmmoniaHCID 1534044-Methoxy-o-phenylenediamineHCID 221617698-Carboxythiomethyl-1-methyl-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 14.7%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

8-Carboxythiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline hydrochloride (27.9 g) and 5-methoxy-o-phenylenediamine (13.8 g) in 4N hydrochloric acid (100 ml) were refluxed for 40 minutes. The reaction mixture was cooled, neutralized with aqueous ammonia and extracted with chloroform. After drying the extract, the solvent was distilled off under reduced pressure and 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 (5.0 g).

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with chloroform
  3. customAfter drying the extract
  4. distillationthe solvent was distilled off under reduced pressure
  5. 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-62963d26e5244183968d03127117918c
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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