m-Chloroperbenzoic acid → (+/-)-1-(Oxiranylmethyl)-2,4-imidazolidinedione

HRID 917288

Reaktionsgleichung

Reaktionsgleichung von HRID 917288
[CH2:1]([N:4]1[CH2:8][C:7](=[O:9])[NH:6][C:5]1=[O:10])[CH:2]=[CH2:3].ClC1C=C(C(OO)=[O:19])C=CC=1.S(=O)(O)[O-]>C(Cl)Cl>[O:19]1[CH2:3][CH:2]1[CH2:1][N:4]1[CH2:8][C:7](=[O:9])[NH:6][C:5]1=[O:10]

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 104748BisulfiteHCID 220209241-(Prop-2-en-1-yl)imidazolidine-2,4-dione

Produkt 1

HCID 22020929(+/-)-1-(Oxiranylmethyl)-2,4-imidazolidinedioneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A reaction solution of 1-(2-propenyl)-2,4-imidazolidinedione (0.036 mol) and 3-chloro-benzenecarboperoxoic acid (0.043 mol, 70.75%) in DCM (25 ml) was stirred for 2 hours at room temperature. An aqueous solution of bisulfite was added (to remove excess 3-chlorobenzenecarboperoxoic acid) and the mixture was stirred for 10 minutes. Na2CO3 was added and this mixture was extracted with DCM. The separated organic layer was dried, filtered and the solvent evaporated, yielding 5 g (89%) of (±)-1-(oxiranylmethyl)-2,4-imidazolidinedione (interm. 1).

Aufarbeitung

  1. custom(to remove excess 3-chlorobenzenecarboperoxoic acid)
  2. additionNa2CO3 was added
  3. extractionthis mixture was extracted with DCM
  4. customThe separated organic layer was dried
  5. filtrationfiltered
  6. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-7944daf78bd94ed1bbf1d811cb1457ed
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273862B2

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