Carbon Dioxide → 3,3-Dinitroazetidinium trifluoromethanesulfonate

HRID 1608674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1608674
C(OC([N:11]1[CH2:14][C:13]([N+:18]([O-:20])=[O:19])([N+:15]([O-:17])=[O:16])[CH2:12]1)=O)C1C=CC=CC=1.C1(OC)C=CC=CC=1.[F:29][C:30]([F:36])([F:35])[S:31]([OH:34])(=[O:33])=[O:32].C(=O)=O>C(Cl)Cl.C(OCC)C>[F:29][C:30]([F:36])([F:35])[S:31]([O-:34])(=[O:33])=[O:32].[N+:15]([C:13]1([N+:18]([O-:20])=[O:19])[CH2:14][NH2+:11][CH2:12]1)([O-:17])=[O:16]

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 7519AnisoleHCID 62406Trifluoromethanesulfonic acidHCID 104464271-Azetidinecarboxylic acid, 3,3-dinitro-, phenylmethyl ester

Produkt 1

HCID 200870453,3-Dinitroazetidinium trifluoromethanesulfonateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(benzyloxycarbonyl)-3,3-dinitroazetidine (8.0 g, 0.028 mole) in 80 ml of methylene chloride containing anisole (9.24 g, 0.08 mole) was added trifluoromethanesulfonic acid (10 g, 0.067 mole), slowly with vigorous stirring at room temperature. Carbon dioxide was evolved and the solution turned light red in color. Stirring was continued for about 30 minutes after the addition. Diethyl ether was added slowly to quench the reaction and precipitate the resultant product. The solids were filtered, washed with diethyl ether and air-dried to give 4.10 g (97% yield) of pure 3,3-dinitroazetidinium trifluoromethanesulfonate. The melting point of the product was 176° (dec.).

Aufarbeitung

  1. stirringStirring
  2. additionafter the addition
  3. customto quench
  4. customthe reaction
  5. customprecipitate the resultant product
  6. filtrationThe solids were filtered
  7. washwashed with diethyl ether
  8. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-59a8979f1dfa4deeb83f8064dc94f4c6
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05395945

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