m-Chloroperbenzoic acid → HCID 18947224, compound

HRID 1769155Notes

Reaction equation

HRID 1769155 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][N:13]([CH3:26])[C:14]1([CH2:24][OH:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[S:17][CH2:16][CH2:15]1>C(Cl)Cl>[CH3:12][N:13]([CH3:26])[C:14]1([CH2:24][OH:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[S:17](=[O:9])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18947221HCID 18947221, compound

Product 1

HCID 18947224HCID 18947224, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

248 mg of 70% m-chloroperbenzoic acid was added to a 20 ml of methylene chloride solution containing 222 mg of 4-dimethylamino-4-hydroxymethyl-2,3-dihydro-4H-1-benzothiopyran dissolved therein, and stirred at room temperature for 30 minutes. The reaction solution was washed with 5% aqueous sodium thiosulfate solution, saturated sodium bicarbonate solution and brine in this order, then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the crystals were recrystallized from a solvent mixture of ethyl acetate and isopropyl ether. 53 mg of the title compound was obtained as colorless crystals. ##STR33## Melting point: 132°-133° C. IR(KBr)cm-1 : 3245, 1070, 1000

Workup

  1. dissolutiondissolved
  2. washThe reaction solution was washed with 5% aqueous sodium thiosulfate solution, saturated sodium bicarbonate solution and brine in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe crystals were recrystallized from a solvent mixture of ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-1edf088ec2834bd598cb438355b22045
Source dataset
uspto-grants-1995_01
Patent number
US05380748

Reaction notes

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