Benzyl azide → HCID 684588, compound

HRID 1274501Notes

Reaction equation

HRID 1274501 reaction equation
[CH2:1]([N:8]=[N+:9]=[N-:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:12](=[CH2:15])[C:13]#[N:14]>O>[CH2:1]([N:8]1[CH:15]=[C:12]([C:13]#[N:14])[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12152Benzyl azideHCID 701982-Chloroacrylonitrile

Product 1

HCID 684588HCID 684588, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of benzyl azide (1.33 g) and 2-chloroacrylonitrile (1.75 g) in water (5 ml) is stirred at about 80° C. for 22 hours, then excess 2-chloroacrylonitrile is distilled off in vacuo. The mixture is cooled to room temperature and the precipitated product is isolated by filtration and washed with water. After drying, the product is obtained in a yield of 1.66 g=90% of theory m.p. 78-79° C. (recrystallization from toluene/hexane).

Workup

  1. distillationexcess 2-chloroacrylonitrile is distilled off in vacuo
  2. temperatureThe mixture is cooled to room temperature
  3. customthe precipitated product is isolated by filtration
  4. washwashed with water
  5. customAfter drying
  6. customthe product is obtained in a yield of 1.66 g=90% of theory m.p. 78-79° C. (recrystallization from toluene/hexane)

Sources & evidence

ORD record
ord-40c17e3d89b6402f8e717ea48e6bd43f
Source dataset
uspto-grants-2000_12
Patent number
US06156907

Reaction notes

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