18-Crown-6 → HCID 54220809, compound

HRID 1759333Notes

Reaction equation

HRID 1759333 reaction equation
Cl[CH2:2][CH:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15][C:16](F)(F)F)=[CH:11][CH:10]=2)[CH2:4]1.[C:20]([O-:23])(=[O:22])[CH3:21].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[C:20]([O:23][CH2:2][CH:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][CH:10]=2)[CH2:4]1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 13038068HCID 13038068, compound

Product 1

HCID 54220809HCID 54220809, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 15 g of II (R1 =CH3, X=Cl), 50 g of potassium acetate, a catalytic amount of 18-crown-6, and 60 ml of dimethylformamide was heated under nitrogen atmosphere at 130° C. for 5 hours. The mixture was poured into ice water and the solid precipitate was collected by filtration. The solid was recrystallized from 1-chlorobutane to give 11 g of 5-acetoxymethyl-3-(4-methylthiophenyl)-2-oxazolidinone (XV, R1 =CH3).

Workup

  1. filtrationthe solid precipitate was collected by filtration
  2. customThe solid was recrystallized from 1-chlorobutane

Sources & evidence

ORD record
ord-c2ffbbba4bdf4bd99fb197d993f07968
Source dataset
uspto-grants-1982_07
Patent number
US04340606

Reaction notes

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