Sodium Nitrate → HCID 117851667, compound

HRID 1752847Notes

Reaction equation

HRID 1752847 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[Na+].[N:6]([C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Br:19])[CH:16]=2)[N:11]([C:20]([O:22][CH3:23])=[O:21])[CH2:10]1)=[N+:7]=[N-:8]>FC(F)(F)C(O)=O>[N:6]([C@@H:9]1[CH2:18][C:17]2[C:12](=[C:13]([N+:1]([O-:4])=[O:2])[CH:14]=[C:15]([Br:19])[CH:16]=2)[N:11]([C:20]([O:22][CH3:23])=[O:21])[CH2:10]1)=[N+:7]=[N-:8]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 71698261HCID 71698261, compound

Product 1

HCID 117851667HCID 117851667, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of sodium nitrate (30 mg, 0.40 mmol) in trifluoroacetic acid (5 mL) was added bromo azide 13 (100 mg, 0.32 mmol). The resulting solution was stirred at 25° C. for 30 min and then concentrated under reduced pressure. The crude product was then dissolved in EtOAc (50 mL) and the organic portion washed sequentially with saturated aqueous sodium hydrogen carbonate (10 mL), NaOH (1 M solution, 10 mL), and water (10 mL), dried with anhydrous Na2SO4, and then concentrated under reduced pressure. It was purified by column chromatography with petroleum ether/EtOAc (6:4 v/v) to give nitro compound 14 (108 mg) as a thick liquid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe crude product was then dissolved in EtOAc (50 mL)
  3. washthe organic portion washed sequentially with saturated aqueous sodium hydrogen carbonate (10 mL), NaOH (1 M solution, 10 mL), and water (10 mL)
  4. dry with materialdried with anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customIt was purified by column chromatography with petroleum ether/EtOAc (6:4 v/v)

Sources & evidence

ORD record
ord-2e782493127f4e8789e63751913403d8
Source dataset
uspto-grants-2015_10
Patent number
US09163038B2

Reaction notes

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