m-Chloroperbenzoic acid → HCID 18780275, compound

HRID 345705Notes

Reaction equation

HRID 345705 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:31])[NH:13][C:14](=[O:30])[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][CH3:29])[CH:17]=2)=[CH:3]1.ClC1C=CC=C(C(OO)=[O:40])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:31])[NH:13][C:14](=[O:30])[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]([CH3:29])=[O:40])[CH:17]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18780292HCID 18780292, compound

Product 1

HCID 18780275HCID 18780275, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

116 mg of the product of Example 96 in 5 ml of dichloromethane were treated at 0° C. with 60 mg of 85% metachloroperbenzoic acid in 5 ml of dichloromethane. The solution was allowed to warm to room temperature and was then stirred for 1 hour. The solution was washed with aqueous sodium bicarbonate and dried. The solution was concentrated and the residue was crystallized from ethyl acetate/hexane to give 84 mg of rac-3-(1-methyl-3-indolyl)-4-[1-(3-methylsulphinylpropyl)-3-indolyl]-1H-pyrrole-2,5-dione, m.p. 140° C.

Workup

  1. washThe solution was washed with aqueous sodium bicarbonate
  2. customdried
  3. concentrationThe solution was concentrated
  4. customthe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-55091c5cadb9477d8d9308ae185893ec
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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