Sodium Hydroxide → 6-(Methylsulfinyl)-benz[cd]indol-2(1H)-one

HRID 484107Notes

Reaction equation

HRID 484107 reaction equation
[CH3:1][S:2][C:3]1[C:4]2[C:5]3[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]=3[CH:13]=[CH:14][CH:15]=2.ClC1C=CC=C(C(OO)=[O:24])C=1.[OH-].[Na+]>C(O)C>[CH3:1][S:2]([C:3]1[C:4]2[C:5]3[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]=3[CH:13]=[CH:14][CH:15]=2)=[O:24]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 197508246-(Methylthio)benz[cd]indol-2(1H)-one

Product 1

HCID 197508326-(Methylsulfinyl)-benz[cd]indol-2(1H)-oneYield 46.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice water cooled stirred suspension of 1.3 g of 6-(methylthio)-benz[cd]indol-2(1H)-one (Example 2) in 25 ml of ethanol is added portionwise over 12 minutes 1.2 g of 85% m-chloroperbenzoic acid at a rate so the temperature is kept below 7° C. Stirring is continued over 1.25 hours. The reaction mixture is poured over crushed ice and 8 ml of 1N sodium hydroxide with stirring. After 15 minutes of additional stirring, the reaction mixture is filtered. The filtrate is extracted with methylene chloride, dried with magnesium sulfate and evaporated to afford 0.65 g of the desired product as a yellow solid, m.p. 178°-185° C.

Workup

  1. customis kept below 7° C
  2. stirringStirring
  3. additionThe reaction mixture is poured
  4. stirringwith stirring
  5. waitAfter 15 minutes of additional stirring
  6. filtrationthe reaction mixture is filtered
  7. extractionThe filtrate is extracted with methylene chloride
  8. dry with materialdried with magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-102f7def5616452d834fbfaa22686bb8
Source dataset
uspto-grants-1993_07
Patent number
US05229411

Reaction notes

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