Carbon Dioxide → 3,3-Dinitroazetidinium trifluoromethanesulfonate

HRID 1608674Notes

Reaction equation

HRID 1608674 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 200870453,3-Dinitroazetidinium trifluoromethanesulfonateYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-59a8979f1dfa4deeb83f8064dc94f4c6
Source dataset
uspto-grants-1995_03
Patent number
US05395945

Reaction notes

Loading…