4-Chlorophenyl Isocyanate → 5-(Chloromethyl)-3-(4-chlorophenyl)-1,3-oxazolidin-2-one

HRID 374486

Reaktionsgleichung

Reaktionsgleichung von HRID 374486
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[CH2:11]([CH:13]1O[CH2:14]1)[Cl:12].[Br-].[Li+].C(P(=[O:31])(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Cl:12][CH2:11][CH:13]1[O:10][C:9](=[O:31])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:14]1

Komponenten

6

Edukt 4

HCID 76934-Chlorophenyl IsocyanateHCID 7835EpichlorohydrinHCID 13138Tributylphosphine oxideHCID 82050Lithium Bromide

Produkt 1

HCID 189972075-(Chloromethyl)-3-(4-chlorophenyl)-1,3-oxazolidin-2-oneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A toluene (10 ml) solution of 5.9 g of 4-chlorophenyl isocyanate and 3.3 ml of epichlorohydrin was added dropwise to a toluene (1 ml) solution of 0.2 g of lithium bromide and 0.42 g of tri-n-butylphosphine oxide at 100° C. The mixture was stirred at the same temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. Ethanol was added to the obtained residue to collect the crystals by filtration. Thus, 8.9 g of the title compound was obtained (yield 93%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionEthanol was added to the obtained residue
  3. customto collect the crystals
  4. filtrationby filtration

Quellen und Nachweise

ORD-Eintrag
ord-1fb353f2d3984f259097bcc6215d6345
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05480899

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