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

HRID 1088813노트

반응식

HRID 1088813 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

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).

후처리

  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)]

출처 및 근거

ORD 기록
ord-df696adb185e4742983da6ba8101c272
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04963566

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