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

HRID 67286

Reaction equation

HRID 67286 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 an a rotary evaporator. The yield of product was essentially quantitative. Its structure was established by infrared and nuclear magnetic resonance spectroscopy. It had nD30 1.4537 and d430 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. customa rotary evaporator

Sources & evidence

ORD record
ord-f0ca0e9fafa44133964a201cb876e151
Source dataset
uspto-grants-1982_08
Patent number
US04346043

Linked notes

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