Octylamine → 2-Propenamide, N-octyl-

HRID 1075282Notes

Reaction equation

HRID 1075282 reaction equation
S([O-])([O-])(=O)=O.[Ca+2].[C:7](Cl)(=[O:10])[CH:8]=[CH2:9].[CH2:12]([NH2:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(N(CC)CC)C>ClCCl>[CH2:12]([NH:20][C:7](=[O:10])[CH:8]=[CH2:9])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 8143OctylamineHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 24497Calcium Sulfate

Product 1

HCID 823702-Propenamide, N-octyl-Yield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 500 ml four-necked flask equipped with a thermometer, mechanical stirrer, calcium sulfate-filled drying tube, and pressure-equalizing addition funnel is charged with a solution of 45.3 g of acryloyl chloride (0.5 mole) in 180 g of dichloromethane. The solution is cooled to 0° C. and to it is then slowly added a mixture of 66.6 g of n-octylamine (0.5 mole), 50.6 g of triethylamine (0.5 mole), and 125 g of dichloromethane, over a period of 2.5 hrs., at such a rate that the temperature does not exceed 5° C. Upon completion of the addition, the mixture is allowed to warm gradually to ambient temperature. The product is then stored at -15° C. overnight to complete crystallization of the byproduct triethylamine hydrochloride. After removal of the salt by filtration, the filtrate is washed successfully with 250 g of deionized water. The product is then dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo to afford 85 g of N-(n-octyl)acrylamide, bp. 119°-120° (3 mm).

Workup

  1. additionfilled
  2. customdrying
  3. additiontube, and pressure-equalizing addition funnel
  4. additionis then slowly added
  5. customdoes not exceed 5° C
  6. additionUpon completion of the addition
  7. temperatureto warm gradually to ambient temperature
  8. waitThe product is then stored at -15° C. overnight
  9. customcrystallization of the byproduct triethylamine hydrochloride
  10. customAfter removal of the salt
  11. filtrationby filtration
  12. washthe filtrate is washed successfully with 250 g of deionized water
  13. dry with materialThe product is then dried over anhydrous magnesium sulfate
  14. filtrationfiltered
  15. customevaporated in vacuo

Sources & evidence

ORD record
ord-d0fc258a42bb431f82e3c3d8f645e149
Source dataset
uspto-grants-1983_07
Patent number
US04395524

Reaction notes

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