m-Chloroperbenzoic acid → HCID 13821853, compound

HRID 1788934Notes

Reaction equation

HRID 1788934 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]1[C:14]([CH2:15][S:16][CH3:17])=[C:13]([CH3:18])[N:12]=[C:7]12.ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]1[C:14]([CH2:15][S:16]([CH3:17])=[O:27])=[C:13]([CH3:18])[N:12]=[C:7]12

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13821843HCID 13821843, compound

Product 1

HCID 13821853HCID 13821853, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 7-chloro-2-methyl-3-methylthiomethylimidazo[2,1-a]isoquinoline (2 g) in chloroform (20 ml) was added portionwise 70% m-chloroperbenzoic acid (1.78 g). After being stirred under ice cooling for 30 minutes, the mixture was washed successively with aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate, treated with activated charcoal and evaporated in vacuo. The residue was purified by column chromatography on silica gel (25 g) with a mixture of chloroform and methanol (50:1) as an eluent to afford a solid. This solid was recrystallized from ethanol to give 7-chloro-2-methyl-3-methylsulfinylmethylimidazo[2,1-a]isoquinoline (1.36 g).

Workup

  1. washthe mixture was washed successively with aqueous sodium bicarbonate, water and brine
  2. dry with materialdried over magnesium sulfate
  3. additiontreated with activated charcoal
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (25 g) with a mixture of chloroform and methanol (50:1) as an eluent
  6. customto afford a solid
  7. customThis solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-111a73a408064d02b9746897538f896a
Source dataset
uspto-grants-1987_08
Patent number
US04686227

Reaction notes

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