Potassium Permanganate → HCID 22603443, compound

HRID 2307924Notes

Reaction equation

HRID 2307924 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([S:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])=[C:7]1[C:23]([O:25][CH2:26][CH3:27])=[O:24].[Mn]([O-])(=O)(=O)=[O:33].[K+]>CC(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([S:15]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)(=[O:33])=[O:16])=[C:7]1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 22603407HCID 22603407, compound

Product 1

HCID 22603443HCID 22603443, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a suspension of ethyl N-(3,4-dichlorobenzyl)-3-morpholinosulphinylindole-2-carboxylate (803 mg) in acetone (40 ml) was added a solution of potassium permanganate (528 mg) in water (15 ml). The resulting mixture was stirred for 18 hours. The mixture was poured into water (20 ml) and extracted with diethyl ether, dried (MgSO4) and concentrated to a gum which was purified by column chromatography using iso-hexane:ethyl acetate (3:1) as eluent to give the desired product (681 mg, 82%); NMR d (CDCl3) 1.3 (t, 3H), 3.2-3.2 (m, 4H), 3.7-3.8 (m, 4H), 5.4 (s, 2H), 6.95 (d, 1H), 7.3-7.4 (m, 5H), 8.05 (d, 1H); M/z (+) 499.2 (MH+), 497.3.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated to a gum which
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b3a743c2e7bf4629838d3ceef1b72b28
Source dataset
uspto-grants-2004_12
Patent number
US06833387B1

Reaction notes

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