m-Chloroperbenzoic acid → 3-[(3-Isopropyl-oxazolidin-2-on-5-yl)methoxy]-6-methyl-pyridine-1-oxide

HRID 1701754Notes

Reaction equation

HRID 1701754 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH:12]([N:15]1[CH2:19][CH:18]([CH2:20][O:21][C:22]2[CH:23]=[N:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[O:17][C:16]1=[O:29])([CH3:14])[CH3:13]>ClCCl>[CH:12]([N:15]1[CH2:19][CH:18]([CH2:20][O:21][C:22]2[CH:23]=[N+:24]([O-:9])[C:25]([CH3:28])=[CH:26][CH:27]=2)[O:17][C:16]1=[O:29])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 204834455-{[(6-Methylpyridin-3-yl)oxy]methyl}-3-(propan-2-yl)-1,3-oxazolidin-2-one

Product 1

HCID 204834313-[(3-Isopropyl-oxazolidin-2-on-5-yl)methoxy]-6-methyl-pyridine-1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.1 g of m-chloroperbenzoic acid in 30 ml of dichloromethane is added over the course of 10 minutes to a solution of 4.8 g of 3-isopropyl-5-[(6-methylpyridin-3-yloxy)methyl]-oxazolidin-2-one in 50 ml of dichloromethane, whilst stirring, and the mixture is left to stand overnight at room temperature. After dilution with 50 ml of dichloromethane the reaction mixture is extracted with 20 ml of saturated potassium bicarbonate solution at a time, dried over sodium sulphate and evaporated in vacuo. The crystalline residue is recrystallised from dichloromethane-ether. 3-[(3-Isopropyloxazolidin-2-on-5-yl)methoxy]-6-methyl-pyridine-1-oxide, thus obtained, melts at 137°-139° C.

Workup

  1. waitthe mixture is left
  2. extractionAfter dilution with 50 ml of dichloromethane the reaction mixture is extracted with 20 ml of saturated potassium bicarbonate solution at a time
  3. dry with materialdried over sodium sulphate
  4. customevaporated in vacuo
  5. customThe crystalline residue is recrystallised from dichloromethane-ether

Sources & evidence

ORD record
ord-ff86da7aa93946d587924b87b2935496
Source dataset
uspto-grants-1980_03
Patent number
US04195090

Reaction notes

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