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

HRID 1088811노트

반응식

HRID 1088811 반응식
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([SH:10])[NH:9][C:5]=2[CH:4]=1.[H-].[Na+].Cl.[CH3:16][N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[CH2:27]Cl)[CH2:20][CH2:19][CH2:18]1>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([S:10][CH2:27][C:25]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:26]=3[N:17]([CH3:16])[CH2:18][CH2:19][CH2:20]4)[NH:9][C:5]=2[CH:4]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 221617911-Methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline hydrochlorideHCID 178488032HCID 178488032, 화합물

생성물 1

HCID 150533328-(5-Methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline수율 49.7%

시약·촉매·용매 2

HCID 2855718-Crown-6촉매HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 5-methoxy-2-mercaptobenzimidazole(0.9 g), sodium hydride (60% in oil, 0.20 g) and 18-crown-6(i.e. 1,4,7,10,13,16-hexaoxacyclooctadecane) (50 mg) in dimethyl formamide (15 ml) was stirred for 20 minutes at room temperature. To the mixture was added a solution of 1-methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline hydrochloride (1.1 g) in dimethyl formamide (15 ml) and the solution was stirred for 20 hours at room temperature. Dimethyl formamide was distilled off, and chloroform, 30% aqueous solution of sodium hydroxide and water were added to the resulting residue. The mixture was stirred for 2 hours and extracted with chloroform. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The resultant 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 (0.80 g).

후처리

  1. distillationDimethyl formamide was distilled off
  2. additionchloroform, 30% aqueous solution of sodium hydroxide and water were added to the resulting residue
  3. stirringThe mixture was stirred for 2 hours
  4. extractionextracted with chloroform
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe resultant residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (4:1)]

출처 및 근거

ORD 기록
ord-ec7016845283424a859cb5b6bb637fa4
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04963566

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