Nonanoyl chloride → N,N-bis(Pelargonoyloxyethyl)pelargonoylacetamide

HRID 358100

Reaction equation

HRID 358100 reaction equation
[C:1](Cl)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[OH:12][CH2:13][CH2:14][N:15]([CH2:20][CH2:21][OH:22])[C:16](=[O:19])[CH2:17]O>N1C=CC=CC=1>[C:1]([O:22][CH2:21][CH2:20][N:15]([CH2:14][CH2:13][O:12][C:1](=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[C:16](=[O:19])[CH2:17][C:1](=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 69819Nonanoyl chlorideHCID 87097N,N-Bis(2-hydroxyethyl)glycolamide

Product 1

HCID 86738544N,N-bis(Pelargonoyloxyethyl)pelargonoylacetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

106 g (0.6 mole) of pelargonoyl chloride was added dropwise with stirring to a solution of 32.6 g (0.2 mole) of N,N-bis(hydroxyethyl)hydroxyacetamide in 60 ml of pyridine. The precipitated pyridine hydrochloride was filtered, washed with benzene, and discarded. The benzene solution of product was water washed, dried over sodium sulfate, and passed through an activated alumina column to remove any acid. The benzene was stripped off on a rotary evaporator. The yield of product was essentially quantitative. Its structure was established by infrared and nuclear magnetic resonance spectroscopy. It had n30D 1.4537 and d304 0.9745.

Workup

  1. filtrationThe precipitated pyridine hydrochloride was filtered
  2. washwashed with benzene
  3. washwashed
  4. dry with materialdried over sodium sulfate
  5. customto remove any acid
  6. customThe benzene was stripped off on a rotary evaporator

Sources & evidence

ORD record
ord-d17743856c89465dbf52a6034e429adb
Source dataset
uspto-grants-1984_08
Patent number
US04464392

Linked notes

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