m-Chloroperbenzoic acid → HCID 22556792, compound

HRID 983989Notes

Reaction equation

HRID 983989 reaction equation
[C:1]1([C:13]2[C:14](=[O:28])[NH:15][C:16](=[O:27])[C:17]=2[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[S:6][CH2:5][CH2:4][N:3]3[CH:2]=1.ClC1C=CC=C(C(OO)=[O:37])C=1.S(=O)(O)[O-].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[NH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([C:17]2[C:16](=[O:27])[NH:15][C:14](=[O:28])[C:13]=2[C:1]2[C:11]3=[C:12]4[C:7](=[CH:8][CH:9]=[CH:10]3)[S:6](=[O:37])[CH2:5][CH2:4][N:3]4[CH:2]=2)=[CH:19]1

Participants

6

Reactant 4

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

Product 1

HCID 22556792HCID 22556792, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3,4-Dihydro-5-thia-2a-aza-acenaphthylen-1-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione (0.50 g, 1.3 mmol) in dichloromethane was added meta-chloroperbenzoic acid (0.224 g, 1.3 mmol) at 0° C. The reaction mixture was stirred for 24 hours at room temperature and a saturated solution of sodium bisulfite and sodium bicarbonate (20 mL) was added. The mixture was extracted with ethyl acetate (2×20 mL). The organic layer was subjected to silica gel chromatography, eluting with ethyl acetate/hexanes (1:1). Fractions containing product were combined and concentrated under reduced pressure to provide 0.168 g (32.3%).of the title compound.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×20 mL)
  2. washeluting with ethyl acetate/hexanes (1:1)
  3. additionFractions containing product
  4. concentrationconcentrated under reduced pressure
  5. customto provide 0.168 g (32.3%)

Sources & evidence

ORD record
ord-bc3a98da04514bf3987e8615e8ed0f89
Source dataset
uspto-grants-2005_03
Patent number
US06867198B2

Reaction notes

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