Potassium glycinate → Oleylmethyldihydroxyethylammonium glycinate

HRID 1461636Notes

Reaction equation

HRID 1461636 reaction equation
[Cl-].[CH2:2]([CH2:20][NH2+:21][CH2:22][CH:23]([OH:25])[OH:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].NCC([O-])=O.[K+]>C(O)C(C)C>[NH2:21][CH2:22][C:23]([O-:25])=[O:24].[CH2:2]([CH2:20][NH2+:21][CH2:22][CH:23]([OH:25])[OH:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 23673715Potassium glycinateHCID 86745345Oleylmethyldihydroxyethylammonium chloride

Product 1

HCID 86745343Oleylmethyldihydroxyethylammonium glycinateYield 193.1%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

A four-necked flask fitted with stirrer and condenser means was charged with 40.5 g of oleylmethyldihydroxyethylammonium chloride, 13 g of potassium glycinate and 200 g of isobutyl alcohol and the reaction was conducted at 40°-50° C. in an atmosphere of nitrogen gas introduced at a low flow rate for 6 hours. The precipitate was then collected by filtration and washed with 30 ml of isobutyl alcohol. The filtrate and the washings were combined and concentrated under reduced pressure. The residue was dissolved in 200 g of toluene and filtered. The filtrate was then concentrated to give 43.1 g (theoretical yield 44.4 g) of oleylmethyldihydroxyethylammonium glycinate as a waxy product. The elemental analysis and infrared absorption data are given below.

Workup

  1. customA four-necked flask fitted with stirrer and condenser means
  2. customwas conducted at 40°-50° C. in an atmosphere of nitrogen gas
  3. additionintroduced at a low flow rate for 6 hours
  4. filtrationThe precipitate was then collected by filtration
  5. washwashed with 30 ml of isobutyl alcohol
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in 200 g of toluene
  8. filtrationfiltered
  9. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-03d8183a1c0442c08c4699066a63a5f4
Source dataset
uspto-grants-1991_12
Patent number
US05076828

Reaction notes

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