Sodium hydride → HCID 22161795, compound

HRID 1088812Notes

Reaction equation

HRID 1088812 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[CH3:13][N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[CH2:24]Cl)[C:17]([CH3:26])=[CH:16][CH2:15]1>CN(C)C=O>[CH3:13][N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[CH2:24][S:1][C:2]2[NH:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)[C:17]([CH3:26])=[CH:16][CH2:15]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 22161766HCID 22161766, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 22161795HCID 22161795, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Mercaptobenzimidazole (0.7 g) was dissolved in dimethyl formamide (30 ml). Sodium hydride (60% in oil, 0.19 g) was added thereto under ice-cooling and the mixture was stirred for 30 minutes. Sequentially, a solution of 1,4-dimethyl-8-chloromethyl-1,2-dihydroquinoline (0.8 g) in dimethyl formamide(5 ml) was added dropwise to the reaction mixture and the mixture was stirred for 1 hour under ice-cooling. After distilling off dimethyl formamide, the resulting residue was poured into an ice-cold water and the mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, then chloroform was distilled off. The resulting residue was purified by silica gel column chromatography [eluent : dichloromethane-methanol (200:1)] to give 1,4-dimethyl-8-(2-benzimidazolyl)thiomethyl-1,2-dihydroquinoline (0.4 g).

Workup

  1. temperatureunder ice-cooling
  2. stirringthe mixture was stirred for 1 hour under ice-
  3. temperaturecooling
  4. distillationAfter distilling off dimethyl formamide
  5. additionthe resulting residue was poured into an ice-cold water
  6. extractionthe mixture was extracted with chloroform
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. distillationchloroform was distilled off
  9. customThe resulting residue was purified by silica gel column chromatography [eluent : dichloromethane-methanol (200:1)]

Sources & evidence

ORD record
ord-a9e0ccbc23bc4446a8b5f7000d6a190d
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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