m-Chloroperbenzoic acid → HCID 18780254, compound

HRID 345706Notes

Reaction equation

HRID 345706 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:32])[NH:13][C:14](=[O:31])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][CH2:26][CH2:27][S:28]([CH3:30])=[O:29])[CH:17]=2)=[CH:3]1.ClC1C=CC=C(C(OO)=[O:41])C=1>ClCCl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:32])[NH:13][C:14](=[O:31])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][CH2:26][CH2:27][S:28]([CH3:30])(=[O:41])=[O:29])[CH:17]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18780275HCID 18780275, compound

Product 1

HCID 18780254HCID 18780254, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

90 mg of the product of Example 97 in 5 ml of dichloromethane were treated with 60 mg of 85% metachloroperbenzoic acid in 5 ml of dichloromethane. The solution was stirred for 2 hours and then washed with aqueous sodium bicarbonate. The solution was dried and concentrated. Chromatography of the residue on silica gel with dichloromethane/ethyl acetate (1:1) and recrystallization from ethyl acetate/hexane gave 25 mg of 3-(1-methyl-3-indolyl)-4-[1-(3-methylsulphonylpropyl)-3-indolyl]-1H-pyrrole-2,5-dione, m.p. 225°-227° C.

Workup

  1. washwashed with aqueous sodium bicarbonate
  2. customThe solution was dried
  3. concentrationconcentrated
  4. customChromatography of the residue on silica gel with dichloromethane/ethyl acetate (1:1) and recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2bf84bb8b2f84a4aac0d7fcd74d7f9d2
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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