Sodium Sulfite → 7-[(Methylsulfonyl)methyl]-1H-indole

HRID 561424Notes

Reaction equation

HRID 561424 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)C=1.CS[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[NH:22][CH:21]=[CH:20]2.[S:24]([O-:27])([O-])=[O:25].[Na+].[Na+]>O1CCCC1>[CH3:2][S:24]([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[NH:22][CH:21]=[CH:20]2)(=[O:27])=[O:25]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583922947-[(Methylsulfonyl)methyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

36.7 g (149 mmol) of 70% pure meta-chloroperbenzoic acid were added to 12.0 g (67.7 mmol) of the compound from Example 8A in 800 ml of tetrahydrofuran at 0° C., and the mixture was stirred at RT for 15 min. Addition of 100 ml of a saturated aqueous sodium sulfite solution was followed by extraction with ethyl acetate several times. The combined organic phases were washed five times with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and concentrated. 11.0 g (75% of theory) of the title compound were obtained.

Workup

  1. extractionwas followed by extraction with ethyl acetate several times
  2. washThe combined organic phases were washed five times with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ce85962082114c189d35e852039d7313
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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