1,2-Dichloroethane → 1-(Dioctadecylamino)methyl-4-carbomethoxy benzene

HRID 258738Notes

Reaction equation

HRID 258738 reaction equation
[CH2:1]([N:19]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]#N)=[CH:41][CH:40]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(Cl)CCl.[CH3:51][OH:52].[OH2:53]>>[CH2:1]([N:19]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]([O:52][CH3:51])=[O:53])=[CH:41][CH:40]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 887MethanolHCID 962WaterHCID 204329871-(Dioctadecylamino)methyl-4-cyanobenzene

Product 1

HCID 204330161-(Dioctadecylamino)methyl-4-carbomethoxy benzeneYield 73.6%

Procedure

The nitrile (15 g.), ethylene dichoride (200 ml.), methanol (50 ml.) and water (20 ml.) are combined and stirred at room temperature. Hydrogen chloride gas is bubbled into the mixture for three hours after which the yellow solution is refluxed for three hours. Methanol (50 ml.) and water (10 ml.) are added and hydrogen chloride bubbled into the mixture for one hour and refluxing continued for 14 hours. Methanol (10 ml.) and water (2 ml.) are added and hydrogen chloride bubbled in for one hour. The mixture is refluxed for four hours, cooled to room temperature and made alkaline by addition of saturated aqueous sodium bicarbonate solution. The ethylene dichloride phase is separated and the aqueous phase extracted with chloroform (2× 100 ml.). The combined organic solutions are washed with water (100 ml.), dried (Na2SO4) and evaporated to give 1-(dioctadecylamino)methyl-4-carbomethoxy benzene (14.0 g., 73.6% yield).

Workup

  1. customHydrogen chloride gas is bubbled into the mixture for three hours after which the yellow solution
  2. temperatureis refluxed for three hours
  3. additionMethanol (50 ml.) and water (10 ml.) are added
  4. customhydrogen chloride bubbled into the mixture for one hour
  5. temperaturerefluxing
  6. additionMethanol (10 ml.) and water (2 ml.) are added
  7. customhydrogen chloride bubbled in for one hour
  8. temperatureThe mixture is refluxed for four hours
  9. temperaturecooled to room temperature
  10. additionby addition of saturated aqueous sodium bicarbonate solution
  11. customThe ethylene dichloride phase is separated
  12. extractionthe aqueous phase extracted with chloroform (2× 100 ml.)
  13. washThe combined organic solutions are washed with water (100 ml.)
  14. dry with materialdried (Na2SO4)
  15. customevaporated

Sources & evidence

ORD record
ord-e54e032ba4014e3a94b22085ea51003a
Source dataset
uspto-grants-1977_07
Patent number
US04034040

Reaction notes

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