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

HRID 1088814노트

반응식

HRID 1088814 반응식
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

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 1534044-Methoxy-o-phenylenediamineHCID 221617698-Carboxythiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline hydrochloride

생성물 1

HCID 150533328-(5-Methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline수율 14.7%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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).

후처리

  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)]

출처 및 근거

ORD 기록
ord-62963d26e5244183968d03127117918c
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04963566

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