Sodium Azide → 6-(Azidomethyl)phenanthridine

HRID 718739Notes

Reaction equation

HRID 718739 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][C:7]1[N:8]=[C:9]2[C:14](=[C:15]3[C:20]=1[CH:19]=[CH:18][CH:17]=[CH:16]3)[CH:13]=[CH:12][CH:11]=[CH:10]2>CC(C)=O>[N:1]([CH2:6][C:7]1[N:8]=[C:9]2[C:14](=[C:15]3[C:20]=1[CH:19]=[CH:18][CH:17]=[CH:16]3)[CH:13]=[CH:12][CH:11]=[CH:10]2)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 856742386-(Bromomethyl)phenanthridine

Product 1

HCID 867124836-(Azidomethyl)phenanthridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium azide (715 mg, 11.0 mmol) was added to a solution of the bromide 6 (301 mg, 1.10 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for 1 hour, then heated to reflux for 2 hours. The reaction mixture was then allowed to cool to room temperature, the excess sodium azide was filtered off, and the solvent was removed under reduced pressure to yield the crude azide 7 as a light yellow crystalline solid, which was used immediately in the next step without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. temperatureto cool to room temperature
  4. filtrationthe excess sodium azide was filtered off
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-db77acfd88524a279d5592adb1161c74
Source dataset
uspto-grants-2015_11
Patent number
US09194802B2

Reaction notes

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