Ammonium Acetate → 6-(Octadecylthio)hexanamide

HRID 398753Notes

Reaction equation

HRID 398753 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]>CN(C)C(=O)C>[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)hexanamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

19.3 Grams of ammonium acetate and 100 ml of N,N-dimethylacetamide were charged in a flask equipped with a stirrer, a condenser and a calcium chloride drying tube and stirred at room temperature. Thereto was slowly added dropwise 21.0 g of 6-(octadecylthio) hexanoic acid chloride, followed by continuing the stirring for 20 hours and, then, stirring with heating at 60° C. by a water bath for 2 hours. The reaction mixture was cooled to room temperature and the precipitated crystal was filtered off under reduced pressure and washed with acetone. The precipitated crystal was filtered off under reduced pressure and washed with distilled water. The crystal was recrystallized from 2-propanol to obtain 16.0 g of the desired product as a white crystal. m.p. 105° C.

Workup

  1. customequipped with a stirrer, a condenser and a calcium chloride drying tube
  2. customstirring for 20 hours
  3. stirringstirring
  4. temperaturewith heating at 60° C. by a water bath for 2 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. filtrationthe precipitated crystal was filtered off under reduced pressure
  7. washwashed with acetone
  8. filtrationThe precipitated crystal was filtered off under reduced pressure
  9. washwashed with distilled water
  10. customThe crystal was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-62580281b96143f3ac14138a950a5b70
Source dataset
uspto-grants-1998_10
Patent number
US05817599

Reaction notes

Loading…