Methyl iodide → HCID 15053211, compound

HRID 1088818Notes

Reaction equation

HRID 1088818 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[NH:21][CH2:20][CH2:19][CH2:18]2)=[O:11].[H-].[Na+].[CH3:25]I>CN(C)C=O>[CH3:25][N:21]1[C:22]2[C:17](=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:12][S:10]([C:2]2[NH:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[O:11])[CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22161796HCID 22161796, compound

Product 1

HCID 15053211HCID 15053211, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-(2-Benzimidazolyl)sulfinylmethyl-1,2,3,4-tetrahydroquinoline (14.9 g) was dissolved in dimethyl formamide (150 ml). Sodium hydride (60% in oil, 2.2 g) was added thereto with stirring under ice-cooling, and the mixture was stirred for 30 minutes. Sequentially, methyl iodide (8.5 g) was added dropwise to the reaction mixture and the mixture was stirred for 5 hours at 70° to 80° C. After distilling off the solvent, the residue was poured into water and the mixture was extracted with chloroform. The residue obtained by distilling off the chloroform was purified by silica gel column chromatography and recrystallized from diethyl ether-n-hexane to give 1-methyl-8-(2-benzimidazolyl)sulfinylmethyl-1,2,3,4-tetrahydroquinoline (2.1 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes
  3. stirringthe mixture was stirred for 5 hours at 70° to 80° C
  4. distillationAfter distilling off the solvent
  5. additionthe residue was poured into water
  6. extractionthe mixture was extracted with chloroform
  7. customThe residue obtained
  8. distillationby distilling off the chloroform
  9. customwas purified by silica gel column chromatography
  10. customrecrystallized from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-ddde2b83c51f4d11bebbab7534019abf
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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