m-Chloroperbenzoic acid → HCID 22556849, compound

HRID 983990Notes

Reaction equation

HRID 983990 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:11](=[O:28])[NH:12][C:13](=[O:27])[C:14]=2[C:15]2[C:25]3=[C:26]4[C:21](=[CH:22][CH:23]=[CH:24]3)S[CH2:19][CH2:18][N:17]4[CH:16]=2)=[CH:2]1.ClC1C=CC=C(C(OO)=O)C=1.[S:40](=[O:43])(O)[O-:41].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[C:11](=[O:28])[NH:12][C:13](=[O:27])[C:14]=2[C:15]2[C:25]3=[C:26]4[C:21](=[CH:22][CH:23]=[CH:24]3)[S:40](=[O:43])(=[O:41])[CH2:19][CH2:18][N:17]4[CH:16]=2)=[CH:2]1

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22556841HCID 22556841, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 22556849HCID 22556849, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(1H-indol-3-yl)-4-(4,5-dihydro-3H-5-thia-2a-aza-acenaphthylen-1-yl)pyrrole-2,5-dione (0.50 g, 1.3 mmol) in dichloromethane was added meta-chloroperbenzoic acid (0.671 g, 3.89 mmol) at 0° C. After 24 hrs at room temperature, a saturated solution of sodium bisulfite and sodium bicarbonate was added, and the mixture was extracted with ethyl acetate. The organic layer was subjected to silica gel chromatography, eluting with ethyl acetate/hexane (4:1) to give 0.120 g (23.8%) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washeluting with ethyl acetate/hexane (4:1)

Sources & evidence

ORD record
ord-d90d68fbb34c41f6b68c2e6d9ce4ae61
Source dataset
uspto-grants-2005_03
Patent number
US06867198B2

Reaction notes

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