Dodecanoyl chloride → Dodecanamide, N-[2-(2-hydroxyethoxy)ethyl]-

HRID 373194Notes

Reaction equation

HRID 373194 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].[C:8](Cl)(=[O:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>ClCCl.C(N(CC)CC)C>[OH:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][C:8](=[O:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 2

HCID 8166Dodecanoyl chlorideHCID 13578Diglycolamine

Product 1

HCID 168575Dodecanamide, N-[2-(2-hydroxyethoxy)ethyl]-Yield 65.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a cooled solution of 11 g of 2-(2-aminoethoxy)-ethanol in 75 ml of dichloromethane and excess triethylamine was added dropwise 13 g of dodecanoyl chloride in 25 ml of dichloromethane. After stirring at room temperature for 3 hours the reaction mixture was concentrated and then diluted with 100 ml of ethyl acetate and 100 ml of water. The organic layer was washed with 2×50 ml of water and brine, dried, filtered and concentrated to give 13.7 g of crude product. Recrystallization from ethyl acetate/hexane gave 11.2 g of product, m.p. 62°-64° C.

Workup

  1. concentrationwas concentrated
  2. additiondiluted with 100 ml of ethyl acetate and 100 ml of water
  3. washThe organic layer was washed with 2×50 ml of water and brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 13.7 g of crude product
  8. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8f8ee140d72b4b269145c76969559aa3
Source dataset
uspto-grants-1992_11
Patent number
US05162315

Reaction notes

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