Water → HCID 21275882, compound

HRID 395237Notes

Reaction equation

HRID 395237 reaction equation
[C:1](Cl)(=O)[CH:2]=C.[CH2:6]([NH2:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[CH2:19](N(CC)CC)C.[OH2:26]>C1COCC1>[CH2:8]([C:7](=[CH2:19])[C:6]([NH2:18])=[O:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 13583Dodecylamine

Product 1

HCID 21275882HCID 21275882, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

Acryloyl chloride (19 g) was dissolved in THF (200 mL) in a 1 L flask and placed in an ice bath. A solution containing dodecylamine (37.1 g), triethylamine (20.2 g) and THF (300 mL) was added dropwise, maintaining the temperature at 5-15° C. After addition the solution was stirred for 5 minutes and the solid was filtered off and discarded. The solvent was removed in vacuo from the mother liquor and methanol (50 mL) was added to the residue. After stirring, water (200 mL) was added and crystals formed. Additional water (200 mL) was added, the solution was stirred for 30 minutes, and the solid was filtered off. The solid was vacuum dried at room temperature to yield 40.3 g.

Workup

  1. customplaced in an ice bath
  2. additionwas added dropwise
  3. additionAfter addition the solution
  4. filtrationthe solid was filtered off
  5. customThe solvent was removed in vacuo from the mother liquor and methanol (50 mL)
  6. additionwas added to the residue
  7. stirringAfter stirring
  8. additionwater (200 mL) was added
  9. customcrystals formed
  10. stirringthe solution was stirred for 30 minutes
  11. filtrationthe solid was filtered off
  12. customdried at room temperature
  13. customto yield 40.3 g

Sources & evidence

ORD record
ord-061ecb57798b4cec827b010478c8a18a
Source dataset
uspto-grants-2003_08
Patent number
US06605270B1

Reaction notes

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