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

HRID 1513550Notes

Reaction equation

HRID 1513550 reaction equation
[CH3:1][NH:2][CH3:3].[O:4]1[CH2:9][CH2:8][O:7][CH2:6][C:5]1=[O:10]>O1CCOCC1>[CH3:1][N:2]([CH3:3])[C:5](=[O:10])[CH2:6][O:7][CH2:8][CH2:9][OH:4]

Participants

4

Reactant 2

HCID 674Dimethylamine2×HCID 18233Dioxanone

Product 1

HCID 167525962-hydroxyethoxy-acetic acid N,N-dimethylamideYield 95.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into a round-bottom flask of the volume of 100 ml are transferred 50 ml dioxane and the solvent is cooled to 5° C. Subsequently 8.1 g (0.18 mole) dimethylamine is absorbed in the solvent at the temperature of 5-10° C. in 20 minutes. To the solution of dimethylamine, 10.2 g (0.1 mole) of [1,4]-dioxane-2-one are added at the same temperature in 5 minutes and the reaction mixture is stirred at room temperature for 2 hours. After the reaction period, the solvent is evaporated in vacuo at the temperature of 50° C. in one hour. Thus 14.1 g (95.9%) of the title product are obtained, which has the purity of 98% as determined by gas chromatography. Optionally the product can be purified by distilling in vacuo (boiling temperature 130-135° C./13 Pa). The raw product is directly suitable for the preparation of 2-chloroethoxy-acetic acid-N,N-dimethyl-amide.

Workup

  1. customInto a round-bottom flask of the volume of 100 ml are transferred
  2. customAfter the reaction period
  3. customthe solvent is evaporated in vacuo at the temperature of 50° C. in one hour

Sources & evidence

ORD record
ord-ca2f942f58004a5195e487db7fea08a9
Source dataset
uspto-grants-2012_07
Patent number
US08217200B2

Reaction notes

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