Sodium Hydroxide → HCID 20029405, compound

HRID 1721829Notes

Reaction equation

HRID 1721829 reaction equation
[CH3:1][N:2]([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][CH2:18][CH2:19][CH:20]([CH2:22][CH3:23])[CH3:21])[CH3:3].Cl[CH2:25][CH:26]([OH:32])[CH2:27][S:28]([O-:31])(=[O:30])=[O:29].[Na+].[OH-].[Na+]>O.C(O)(C)C>[CH3:3][N+:2]([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][CH2:18][CH2:19][CH:20]([CH2:22][CH3:23])[CH3:21])([CH2:25][CH:26]([OH:32])[CH2:27][S:28]([O-:31])(=[O:30])=[O:29])[CH3:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 23662382Sodium 3-chloro-2-hydroxypropylsulfonateHCID 54431227HCID 54431227, compound

Product 1

HCID 20029405HCID 20029405, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent3×

Procedure

A 1-L round bottom flask (equipped with a magnetic stirrer and reflux condenser) was charged with 20 g (61 mmol) of N,N-dimethyl-(2-butyl)hexadecylamine, 20 g (100 mmol) of sodium 3-chloro-2-hydroxy-1-propanesulfonate, 140 mL isopropanol, 50 mL of water, and 0.6 g (8 mmol) of 50% sodium hydroxide. The mixture was stirred at reflux. The progress of the reaction was followed using a Waters Associates C-18 μ-Bondapak reverse-phase column, 1.5 mL/min of a 10:1 isopropanol:water as solvent and a refractive index detector. Total reflux time was 56 hours. The reaction mixture was extracted with chloroform (200 mL). The organic layer was concentrated in vacuum to give a white solid which was taken up in 600 mL of a 1:1 isopropanol:water mixture and washed with petroleum ether (2 times using 200 mL of petroleum ether).

Workup

  1. customA 1-L round bottom flask (equipped with a magnetic stirrer and reflux condenser)
  2. temperatureat reflux
  3. extractionThe reaction mixture was extracted with chloroform (200 mL)
  4. concentrationThe organic layer was concentrated in vacuum
  5. customto give a white solid which
  6. washwater mixture and washed with petroleum ether (2 times using 200 mL of petroleum ether)

Sources & evidence

ORD record
ord-17fdd0f0a355454f9ec9302e13b6591e
Source dataset
uspto-grants-1989_08
Patent number
US04853138

Reaction notes

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