Acetic Acid → HCID 21528753, compound

HRID 1658183Notes

Reaction equation

HRID 1658183 reaction equation
C(O)(=O)C.[CH2:5]([NH2:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:14]1([CH3:21])[C:15]([CH3:20])=[CH:16][CH:17]=[CH:18][CH:19]=1.C1(SCl)CCCCC1.[CH2:30]([N:32](CC)CC)[CH3:31]>C1C=CC=CC=1.O>[CH2:5]([NH:13][C:30](=[N:32][CH2:20][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:14][CH3:21])[CH3:31])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 7237O-XyleneHCID 8143OctylamineHCID 8471TriethylamineHCID 87312Cyclohexanesulfenyl chloride2×

Product 1

HCID 21528753HCID 21528753, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent2×

Procedure

In like manner a mixture comprising 120 grams (2.0 moles) of anhydrous acetic acid and 314 grams (4.3 mole) of n-octylamine along with 200 cc. of xylene is placed in a 1 liter flask equipped with a Dean-Stark water trap. The flask is then heated to reflux and maintained thereat for a period of 3 hours, the water of condensation which is formed during the reaction being continuously removed from the system. At the end of the 3-hour period, the temperature of the flask is increased until the xylene solvent has been distilled off. Upon recovery of the solvent, the reaction mixture is then allowed to cool to room temperature and transferred to a separate flask. The N,N'-dioctylacetamidine which is prepared thusly is then placed in a flask along with triethylamine and a benzene solvent following which the flask is then cooled to a temperature of 0° C. Upon reaching this reduced temperature, the mixture is treated by slowly adding dropwise an equimolar amount of cyclohexanesulfenyl chloride, the temperature of the solution being maintained in a range of from 0° to 10° C. Upon completion of the addition of the cyclohexanesulfenyl chloride which is accompanied by continuous stirring, the mixture is allowed to return to room temperature while maintaining the stirring thereof. At the end of a 1-hour period, the solid which is formed is washed with benzene and air dried for a period of 24 hours. The solution is then washed with water, dried over magnesium sulfate and the benzene solvent is removed by vacuum. Upon further standing, the desired product comprising N,N'-dioctyl-N-cyclohexylthioacetamidine will crystallize out and may be then recrystallized from an isopropyl-ethyl acetate solution.

Workup

  1. temperatureThe flask is then heated
  2. temperatureto reflux
  3. temperaturemaintained
  4. customis formed during the reaction
  5. custombeing continuously removed from the system
  6. temperatureAt the end of the 3-hour period, the temperature of the flask is increased until the xylene solvent
  7. distillationhas been distilled off
  8. customtransferred to a separate flask
  9. additionthe mixture is treated
  10. temperaturethe temperature of the solution being maintained in a range of from 0° to 10° C
  11. customto return to room temperature
  12. temperaturewhile maintaining the stirring thereof
  13. customAt the end of a 1-hour period, the solid which is formed
  14. washis washed with benzene and air
  15. customdried for a period of 24 hours
  16. washThe solution is then washed with water
  17. dry with materialdried over magnesium sulfate
  18. customthe benzene solvent is removed by vacuum
  19. customwill crystallize out
  20. custommay be then recrystallized from an isopropyl-ethyl acetate solution

Sources & evidence

ORD record
ord-e99251082c124c16a9abe0e224e22d90
Source dataset
uspto-grants-1976_06
Patent number
US03963683

Reaction notes

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