3-(4-Azidophenyl)prop-2-enoyl chloride → HCID 86739435, compound

HRID 544701Notes

Reaction equation

HRID 544701 reaction equation
[N:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10](Cl)=[O:11])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[CH2:15]([NH:17][N:18]([NH:22][CH2:23][CH3:24])[CH2:19][CH2:20][NH2:21])[CH3:16]>C(Cl)(Cl)Cl>[CH2:15]([NH:17][N:18]([NH:22][CH2:23][CH3:24])[CH2:19][CH2:20][NH:21][C:10](=[O:11])[CH:9]=[CH:8][C:7]1[CH:13]=[CH:14][C:4]([N:1]=[N+:2]=[N-:3])=[CH:5][CH:6]=1)[CH3:16]

Participants

4

Reactant 2

HCID 541587253-(4-Azidophenyl)prop-2-enoyl chlorideHCID 86739436HCID 86739436, compound

Product 1

HCID 86739435HCID 86739435, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Subsequently, 8.5 g (40 millimoles) of the p-azidocinnamic acid chloride was dissolved in chloroform, and 4.8 g (40 millimoles) of N,N-diethylaminoethylenediamine was added thereto at a reaction temperature of 10° to 20° C., after which the resulting solution was further allowed to react for 1 hour. The chloroform was distilled off under reduced pressure, and 100 ml of water was added to the resulting oily substance, after which a solution of 1.7 g of sodium hydroxide in 20 ml of water was added thereto on an ice bath. The organic layer separated was extracted with chloroform, and the extract was further washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 11 g of an oily substance as the distillation residue. This oily substance decomposed at 130° C. with formation of bubbles and generation of heat. This oily substance was identified as the compound of this invention by analysis using the following spectral means: ##STR115##

Workup

  1. customat a reaction temperature of 10° to 20° C.
  2. customto react for 1 hour
  3. distillationThe chloroform was distilled off under reduced pressure, and 100 ml of water
  4. additionwas added to the resulting oily substance
  5. additionafter which a solution of 1.7 g of sodium hydroxide in 20 ml of water was added
  6. customThe organic layer separated
  7. extractionwas extracted with chloroform
  8. washthe extract was further washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off
  11. customto obtain 11 g of an oily substance as the distillation residue
  12. customdecomposed at 130° C. with formation of bubbles and generation
  13. temperatureof heat

Sources & evidence

ORD record
ord-01e81f161a66414d894b69b6bc87c26b
Source dataset
uspto-grants-1984_05
Patent number
US04451551

Reaction notes

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