Dimethylamine, hydrochloride → 2-hydroxyethoxy-acetic acid N,N-dimethylamide

HRID 1513554Notes

Reaction equation

HRID 1513554 reaction equation
[Na+].[OH:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([O-:9])=O.[Na].C(O)CO.ClCC([O-])=O.[Na+].Cl.[CH3:22][NH:23][CH3:24].CN(C)C(=O)COCCCl>C1(C)C=CC=CC=1>[CH3:22][N:23]([CH3:24])[C:7](=[O:9])[CH2:6][O:5][CH2:4][CH2:3][OH:2]

Participants

7

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 167525952-chloroethoxy-acetic acid-N,N-dimethylamideHCID 23665015Sodium 2-(2-hydroxyethoxy)acetateHCID 23665759Sodium chloroacetateHCID 86592871Ethylene glycol monosodium salt

Product 1

HCID 167525962-hydroxyethoxy-acetic acid N,N-dimethylamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

200.4 g (1 mol) of crude 2-hydroxyethoxy-acetic acid sodium salt prepared from ethylene glycol monosodium salt and 69 weight % sodium chloroacetate are placed into a 1000 ml round bottom flask equipped with stirrer. 81.5 g (1 mole) of commercial dimethylamine hydrochloride having approximately 8 weight % moisture are added. The reaction mixture is heated to the temperature of 130° C. and is kept at this temperature for 20 minutes. After this period, 400 ml of toluene are added to the reaction mixture and by boiling the azeotropic mixture for a period of 16 hours, the water is separated. After cooling the reaction mixture, sodium chloride is filtered off and the crystals are washed twice with 20 ml toluene each. The toluene phases are combined and the product is isolated by evaporating the toluene. Yield 116.2 g (78.9%) of the title compound having the purity greater than 96% by gas chromatography. The product thus obtained is directly suitable for the conversion into 2-chloroethoxy-acetic acid-N,N-dimethylamide.

Workup

  1. customare placed into a 1000 ml round bottom flask
  2. customequipped with stirrer
  3. waitAfter this period
  4. customof 16 hours
  5. customthe water is separated
  6. temperatureAfter cooling the reaction mixture, sodium chloride
  7. filtrationis filtered off
  8. washthe crystals are washed twice with 20 ml toluene each
  9. customthe product is isolated
  10. customby evaporating the toluene
  11. customThe product thus obtained

Sources & evidence

ORD record
ord-0234e62e636b4586a5eeb6e4af830cfe
Source dataset
uspto-grants-2012_07
Patent number
US08217200B2

Reaction notes

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