Toluene → 2-Phenylazirine

HRID 256803Notes

Reaction equation

HRID 256803 reaction equation
[N:1]([C:4]1(C=CC=CC1)C=C)=[N+]=[N-].[C:12]1([CH3:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:12]1([C:18]2[NH:1][CH:4]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 197840931-Azidostyrene

Product 1

HCID 190986582-Phenylazirine

Procedure

200 ml of toluene was added to the 1-azidostyrene, the mixture was heated under reflux for 1 hour, and the toluene was distilled off under reduced pressure, to obtain 11.2 g of 2-phenylazirin (C) 13.5 g of Compound (A) and 3.6 g of Compound (C) were dissolved in 50 ml of acetone, and then 0.05 g of nickel acetylacetonate was added followed by stirring for 3 hours at room temperature. After distilling the acetone off from the reaction liquid, the residue was purified by silica gel chromatography (eluent: n-hexane/ethyl acetate =3/1), to obtain 12.5 g of Exemplified Coupler (60).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. distillationthe toluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-07cc719b46484c598e9cd5b79675d980
Source dataset
uspto-grants-1993_11
Patent number
US05260181

Reaction notes

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