Benzyl azide → HCID 684588, compound

HRID 651245Notes

Reaction equation

HRID 651245 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-b507592ff39b458db1a838d5381b367f
Source dataset
uspto-grants-2001_08
Patent number
US06277999B1

Reaction notes

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