Propylene Glycol → Octadecyldimethyl [3-(2-pyrrolidonyl)propyl]ammonium tosylate

HRID 476546Notes

Reaction equation

HRID 476546 reaction equation
C(O)C(O)C.[CH2:6]([O:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[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].[CH3:35][N:36]([CH2:38][CH2:39][CH2:40][N:41]1[CH2:45][CH2:44][CH2:43][C:42]1=[O:46])[CH3:37]>>[S:25]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)([O-:27])(=[O:26])=[O:24].[CH2:6]([N+:36]([CH3:35])([CH3:37])[CH2:38][CH2:39][CH2:40][N:41]1[CH2:45][CH2:44][CH2:43][C:42]1=[O:46])[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 3

HCID 1030Propylene GlycolHCID 818482-Pyrrolidinone, 1-[3-(dimethylamino)propyl]-HCID 229551Octadecyl p-Toluenesulfonate

Product 1

HCID 86743541Octadecyldimethyl [3-(2-pyrrolidonyl)propyl]ammonium tosylate

Conditions

Temperature
100 °C

Procedure

To a 100 ml round bottom flask equipped with a thermometer and stirrer containing 167 g. of propylene glycol was added 50.7 g. of octadecyl-p-toluenesulfonate and 20.9 g. of [(dimethylamino)propyl]-2-pyrrolidone. The mixture was heated to 100° C. and stirred at that temperature for 6 hours after which it was cooled and recovered. Analysis by quaternary tetraphenyl boron indicated 22% activity corresponding to a 74% conversion.

Workup

  1. customTo a 100 ml round bottom flask equipped with a thermometer and stirrer
  2. additioncontaining 167 g
  3. temperaturewas cooled
  4. customrecovered

Sources & evidence

ORD record
ord-8387e17c5ae8486dbaf3b26e0530a509
Source dataset
uspto-grants-1989_12
Patent number
US04885158

Reaction notes

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