Diethylethanolamine → HCID 54248583, compound

HRID 544702Notes

Reaction equation

HRID 544702 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]([N:17]([CH2:21][CH3:22])[CH2:18][CH2:19][OH:20])[CH3:16]>C(Cl)(Cl)Cl>[N:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([O:20][CH2:19][CH2:18][N:17]([CH2:21][CH3:22])[CH2:15][CH3:16])=[O:11])=[CH:6][CH:5]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 7497DiethylethanolamineHCID 541587253-(4-Azidophenyl)prop-2-enoyl chloride

Product 1

HCID 54248583HCID 54248583, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 80 g of chloroform was dissolved 6.2 g (30 millimoles) of the p-azidocinnamic acid chloride obtained in Example 16, and 3.5 g (30 millimoles) of 2-diethylaminoethanol was added dropwise while maintaining the solution temperature at 10° to 20° C., after which the resulting mixture was 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 1.3 g of sodium hydroxyde 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 7.2 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. ##STR117##

Workup

  1. additionwas added dropwise
  2. temperaturewhile maintaining the solution temperature at 10° to 20° C.
  3. customto react for 1 hour
  4. distillationThe chloroform was distilled off under reduced pressure, and 100 ml of water
  5. additionwas added to the resulting oily substance
  6. additionafter which a solution of 1.3 g of sodium hydroxyde in 20 ml of water was added
  7. customThe organic layer separated
  8. extractionwas extracted with chloroform
  9. washthe extract was further washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe solvent was distilled off
  12. customto obtain 7.2 g of an oily substance as the distillation residue
  13. customdecomposed at 130° C. with formation of bubbles and generation
  14. temperatureof heat

Sources & evidence

ORD record
ord-b0a5c707405b4228b1da770ef0fb9a7c
Source dataset
uspto-grants-1984_05
Patent number
US04451551

Reaction notes

Loading…