Hydrochloric Acid → N-Octadecanoylacrylamide

HRID 841109Notes

Reaction equation

HRID 841109 reaction equation
[C:1](Cl)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:21]([NH2:25])(=[O:24])[CH:22]=[CH2:23].Cl>[Cl-].[Zn+2].[Cl-].CC(C)=O>[C:1]([NH:25][C:21](=[O:24])[CH:22]=[CH2:23])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6579AcrylamideHCID 8212Stearoyl chloride

Product 1

HCID 22620855N-Octadecanoylacrylamide

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 180AcetoneSolvent

Procedure

Into a 250 -mL-capacity conical flask equipped with an anhydrous calcium chloride (CaCl2) guard tube, 15.1 g 1-octadecanoyl chloride [CH3—(CH2)16—COCl] (0.005 M). 3.5 g acrylamide (CH2═CH—CO—NH2) (0.05 M), and 50 ml acetone were placed to obtained a clear solution. The solution was stirred with a magnetic needle at room temperature. Anhydrous zinc chloride (ZnCl2), 6.5 g (0.05 M), was added and the reaction mixture was stirred at room temperature. After 5-10 min of stirring, vigorous evolution of hydrogen chloride took place which ceased after about 5 min. The temperature of reaction mixture was increased to 40-50° C. It was then cooled to room temperature and poured into 500 ml cold distilled water. A white product precipitated. The product was isolated and purified by reprecipitation from acetone into cold water. The purified product was dried in a vacuum desiccator.

Workup

  1. customInto a 250 -mL-capacity conical flask equipped with an anhydrous calcium chloride (CaCl2) guard tube
  2. customto obtained a clear solution
  3. stirringthe reaction mixture was stirred at room temperature
  4. stirringAfter 5-10 min of stirring
  5. customThe temperature of reaction mixture
  6. temperaturewas increased to 40-50° C
  7. temperatureIt was then cooled to room temperature
  8. additionpoured into 500 ml
  9. distillationcold distilled water
  10. customA white product precipitated
  11. customThe product was isolated
  12. custompurified by reprecipitation from acetone into cold water
  13. customThe purified product was dried in a vacuum desiccator

Sources & evidence

ORD record
ord-61f5b8dc43de47549b7bf44a6c4547d3
Source dataset
uspto-grants-2002_04
Patent number
US06369249B1

Reaction notes

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