Thionyl Chloride → 3-(4-Azidophenyl)prop-2-enoyl chloride

HRID 544700Notes

Reaction equation

HRID 544700 reaction equation
[N:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10](O)=[O:11])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].S(Cl)([Cl:17])=O>>[N:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([Cl:17])=[O:11])=[CH:6][CH:5]=1)=[N+:2]=[N-:3]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 53831969HCID 53831969, compound

Product 1

HCID 541587253-(4-Azidophenyl)prop-2-enoyl chlorideYield 79.2%

Procedure

To 17 g (90 millimoles) of p-azidocinnamic acid was added 53 g (450 millimoles) of thionyl chloride, and the resulting solution was refluxed with heating. When the generation of SO2 gas terminated, the reflux was stopped, after which the excess thionyl chloride was distilled off under reduced pressure to obtain 14.8 g of p-azidocinnamic acid chloride as the distillation residue.

Workup

  1. temperaturethe resulting solution was refluxed
  2. temperaturewith heating
  3. customWhen the generation of SO2 gas terminated
  4. distillationafter which the excess thionyl chloride was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f9beb24956c844e3aa9e0e104b7f9631
Source dataset
uspto-grants-1984_05
Patent number
US04451551

Reaction notes

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