m-Chloroperbenzoic acid → HCID 53951018, compound

HRID 1417505Notes

Reaction equation

HRID 1417505 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([N:19]1[C:31]2[C:30]([S:32][CH3:33])=[C:29]([CH2:34][C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36])[CH:28]=[C:27]([CH3:41])[C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O>[CH2:12]([N:19]1[C:31]2[C:30]([S:32]([CH3:33])=[O:9])=[C:29]([CH2:34][C:35]([O:37][CH:38]([CH3:39])[CH3:40])=[O:36])[CH:28]=[C:27]([CH3:41])[C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54487225HCID 54487225, compound

Product 1

HCID 53951018HCID 53951018, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

750 mg of 80% v/v m-chloroperbenzoic acid in water was added gradually to 40 ml of a solution of isopropyl (9-benzyl-1-methylthio-4-methylcarbazol-2-yl)acetate (1.00 g), obtained in a manner similar to that of the title compound of Example 115, in methylene chloride, and the reaction mixture was stirred for 1 hour, with ice-cooling. After this time, the reaction mixture was diluted with an excess of ethyl acetate and washed with a saturated aqueous solution of sodium hydrogen-carbonate. The resulting organic layer was dried over anhydrous sodium sulfate and then the solvent was removed by evaporation under reduced pressure. The residue was subjected to column chromatography (eluent: a 50-60% v/v solution of ethyl acetate in hexane) to yield 719 mg of the title compound as a solid.

Sources & evidence

ORD record
ord-6292e53fbf96401a8dcdf88234b92c99
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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