Water → N,N'-di(carboxymethyl)-N,N'-dimethyl-N,N'-dilaurylethylenediammonium dihydroxide

HRID 271046Notes

Reaction equation

HRID 271046 reaction equation
[CH3:1][N:2]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:3][CH2:4][N:5]([CH3:18])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].I[CH2:32][C:33]([O-:35])=[O:34].[Na+].[CH:37]([OH:40])([CH3:39])C.[OH2:41]>>[OH-:34].[OH-:40].[C:33]([CH2:32][N+:5]([CH3:18])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:4][CH2:3][N+:2]([CH2:39][C:37]([OH:40])=[O:41])([CH3:1])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([OH:35])=[O:34]

Participants

5

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 5239Sodium IodoacetateHCID 10693647N,N'-dimethyl-N,N'-dilaurylethylenediamine

Product 1

HCID 23137563N,N'-di(carboxymethyl)-N,N'-dimethyl-N,N'-dilaurylethylenediammonium dihydroxide

Conditions

Temperature
80 °C

Procedure

To a 250 mL three-necked flask equipped with a magnetic stirrer, reflux condenser, thermometer and nitrogen purge were added 20 g (0.0472 mole) of N,N′-dimethyl-N,N′-dilaurylethylenediamine, 25.54 g (0.1180 mole) of sodium iodoacetate, 80 mL of isopropanol, and 8 mL of deionized water at ambient temperature. The mixture was heated with stirring to 80° C. and maintained at that temperature for 4.5 hrs. After cooling to room temperature, the solvent was removed under vacuum with a rotary evaporator. Addition of isopropanol (about 100 mL), vacuum filtration, and subsequent removal of isopropanol under vacuum with a rotary evaporator yielded pure N,N′-di(carboxymethyl)-N,N′-dimethyl-N,N′-dilaurylethylenediammonium dihydroxide inner salt, shown as Example 16 in Table 3. Additional bis betaines may be prepared and characterized using procedures similar to those described above. Some of these are shown in Table 3, in which the compounds have the following structure.

Workup

  1. customTo a 250 mL three-necked flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. customthermometer and nitrogen purge
  4. temperatureThe mixture was heated
  5. temperaturemaintained at that temperature for 4.5 hrs
  6. temperatureAfter cooling to room temperature
  7. customthe solvent was removed under vacuum with a rotary evaporator
  8. additionAddition of isopropanol (about 100 mL), vacuum filtration, and subsequent removal of isopropanol under vacuum
  9. customwith a rotary evaporator

Sources & evidence

ORD record
ord-a9e6a28f2e654c74833fbfde4802413a
Source dataset
uspto-grants-2008_11
Patent number
US07452848B2

Reaction notes

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