Ammonium Acetate → 6-(Octadecylthio)hexanamide

HRID 634605Notes

Reaction equation

HRID 634605 reaction equation
C([O-])(=O)C.[NH4+:5].[CH2:6]([S:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](Cl)=[O:31])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CC(N(C)C)=O>[CH2:6]([S:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([NH2:5])=[O:31])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 53857071HCID 53857071, compound

Product 1

HCID 212601376-(Octadecylthio)hexanamideYield 79.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In a 300 ml flask equipped with a stirrer, a condenser and a calcium chloride dryer tube were charged 19.3 g of ammonium acetate and 100 ml of DMAc, and the mixture was stirred at room temperature. Then, to the solution was gradually added dropwise 21.0 g of 6-(octadecylthio)hexanoic acid chloride and stirring of the mixture was continued for further 20 hours. The mixture was stirred at 60° C. for further 2 hours on a hot water bath. After cooling the reaction mixture to room temperature, the precipitated crystals were collected by filtration under reduced pressure and washed with acetone. The resulting crystals were collected by filtration under reduced pressure and washed with distilled water and recrystallized from IPA to obtain 16.0 g of the title compound as white crystals. Melting point: 105° C.

Workup

  1. customIn a 300 ml flask equipped with a stirrer, a condenser and a calcium chloride dryer tube
  2. stirringstirring of the mixture
  3. stirringThe mixture was stirred at 60° C. for further 2 hours on a hot water bath
  4. temperatureAfter cooling the reaction mixture to room temperature
  5. filtrationthe precipitated crystals were collected by filtration under reduced pressure
  6. washwashed with acetone
  7. filtrationThe resulting crystals were collected by filtration under reduced pressure
  8. washwashed with distilled water
  9. customrecrystallized from IPA

Sources & evidence

ORD record
ord-0e7a2c4815fd4a6fb2902c866077cf43
Source dataset
uspto-grants-2001_02
Patent number
US06184180B2

Reaction notes

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