Sodium Bicarbonate → 3,3-Dinitroazetidine

HRID 1608675Notes

Reaction equation

HRID 1608675 reaction equation
FC(F)(F)S([O-])(=O)=O.[N+:9]([C:12]1([N+:16]([O-:18])=[O:17])[CH2:15][NH2+:14][CH2:13]1)([O-:11])=[O:10].C(=O)(O)[O-].[Na+]>O>[N+:9]([C:12]1([N+:16]([O-:18])=[O:17])[CH2:15][NH:14][CH2:13]1)([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 200870453,3-Dinitroazetidinium trifluoromethanesulfonate

Product 1

HCID 52317063,3-DinitroazetidineYield 99.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,3-dinitroazetidinium trifluoromethanesulfonate (2.0 g, 0.0067 mole) was dissolved in 20 ml of water and neutralized with sodium bicarbonate (0.62 g, 0.0074 mole). The free base was extracted into chloroform (3×5 ml) and dried over sodium sulfate. The chloroform was removed under vacuum to quantitatively give the resultant product, 3,3-dinitroazetidine (0.98 g) as a colorless to light yellow oil.

Workup

  1. extractionThe free base was extracted into chloroform (3×5 ml)
  2. dry with materialdried over sodium sulfate
  3. customThe chloroform was removed under vacuum

Sources & evidence

ORD record
ord-7837106806a34100af7d543e9875d3d2
Source dataset
uspto-grants-1995_03
Patent number
US05395945

Reaction notes

Loading…