4-Toluenesulfonyl chloride → 2-Chloromethyl-6-methanesulphonamidoquinoline

HRID 467105Notes

Reaction equation

HRID 467105 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N+:12]([O-])=[C:11]([CH3:17])[CH:10]=[CH:9]2)(=[O:4])=[O:3].C1(C)C=CC(S([Cl:27])(=O)=O)=CC=1>ClCCCl>[Cl:27][CH2:17][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][CH:15]=[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:7]=2)[N:12]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 198134366-Methanesulphonamido-2-methylquinoline-1-oxide

Product 1

HCID 190455722-Chloromethyl-6-methanesulphonamidoquinoline

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

6-Methanesulphonamido-2-methylquinoline-1-oxide (1.65 g) and p-toluenesulphonyl chloride (1.72 g) were heated under reflux for 1 hour in 1,2-dichloroethane solution, and the reaction mixture was then stood at room temperature for 17 hours. The reaction mixture was then washed twice with aqueous sodium bicarbonate, dried (MgSO4) and evaporated in vacuo. The residue was purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 1%). The product-containing fractions were combined and evaporated to give a gum which solidified when triturated with ether. Recrystallisation from toluene gave the title compound, yield 0.75 g, m.p. 160°-162°.

Workup

  1. washThe reaction mixture was then washed twice with aqueous sodium bicarbonate
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica eluting with methylene chloride
  5. additioncontaining methanol (0% up to 1%)
  6. customevaporated
  7. customto give a gum which
  8. customtriturated with ether
  9. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-0c990950c7f94641a1807900385b8514
Source dataset
uspto-grants-1992_10
Patent number
US05158964

Reaction notes

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