Benzyl Chloride → HCID 86739287, compound

HRID 1388871Notes

Reaction equation

HRID 1388871 reaction equation
[CH2:1]([NH2:19])[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].[CH2:20]([OH:22])[CH3:21].[CH2:23]([OH:25])[CH3:24].[CH2:26]([Cl:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)(O)[O-].[Na+]>C(O)(C)C>[Cl-:33].[CH2:26]([NH2+:19][CH2:1][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:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH2:20]([OH:22])[CH3:21].[CH2:23]([OH:25])[CH3:24]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 516892Sodium BicarbonateHCID 86739288HCID 86739288, compound

Product 1

HCID 86739287HCID 86739287, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 4-liter reaction vessel equipped with a reflux condenser and mechanical stirrer was charged with 719.6 gm. (2.0 mol) diethanol octadecylamine, 278.5 gm. (2.2 mol) benzyl chloride, 20 gm. of sodium bicarbonate and approximately 400 ml. isopropyl alcohol. The reaction mixture was heated under reflux overnight. An aliquot was removed, analyzed and found to contain 7.4% amine and 1.7% amine HCl. The mixture was allowed to continue reacting overnight. A second aliquot was analyzed and found to contain 4.1% amine and 3.7% amine HCl. An additional 20 gm. of sodium bicarbonate and 30 gm. benzyl chloride were added. After one week the reaction had not progressed any further. The mixture was placed in the autoclave and the quaternization was finished with methyl chloride. The final analyses showed amine 0.0%; amine HCl <1% and Effective gram MW 834.4.

Workup

  1. customA 4-liter reaction vessel
  2. customequipped with a reflux condenser and mechanical stirrer
  3. additionwas charged with 719.6 gm
  4. temperatureThe reaction mixture was heated
  5. temperatureunder reflux overnight
  6. customAn aliquot was removed
  7. additionbenzyl chloride were added
  8. waitAfter one week the reaction had not progressed

Sources & evidence

ORD record
ord-ed9e41cefed24629aae94f3b7786c93a
Source dataset
uspto-grants-1984_02
Patent number
US04434076

Reaction notes

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