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

HRID 1088811Notes

Reaction equation

HRID 1088811 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent2×

Procedure

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).

Workup

  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)]

Sources & evidence

ORD record
ord-ec7016845283424a859cb5b6bb637fa4
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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