Ethanolamine → HCID 20026677, compound

HRID 1723036Notes

Reaction equation

HRID 1723036 reaction equation
[CH3:1][C:2]1O[C:4]([CH3:7])=[N:5][N:6]=1.[CH2:8]([CH2:10][NH2:11])[OH:9]>CN1CCCC1=O>[CH3:1][C:2]1[N:11]([CH2:10][CH2:8][OH:9])[C:4]([CH3:7])=[N:5][N:6]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 47363912,5-dimethyl-1,3,4-oxadiazole

Product 1

HCID 20026677HCID 20026677, compoundYield 49,585.199%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

2,5-Dimethyl-1,3,4-oxadiazole (19.7 g, 0.2 mmole) and ethanolamine (18.3 g, 0.3 mole) were dissolved in 1-methyl-2-pyrrolidinone (20 ml) and the stirred reaction mixture heated at 160° C. for 24 hours, then cooled to ambient temperature. The residual gum was chromatographed on silica eluting with ethyl acetate containing from 20% to 50% methanol. Evaporation of the appropriate fractions and trituration of the residual foam with ethyl acetate gave the title product (14 g, 50%).

Workup

  1. customthe stirred reaction mixture
  2. temperaturecooled to ambient temperature
  3. customThe residual gum was chromatographed on silica eluting with ethyl acetate containing from 20% to 50% methanol
  4. customEvaporation of the appropriate fractions and trituration of the residual foam with ethyl acetate

Sources & evidence

ORD record
ord-2732fdbb68164b65a78042d9e0a38abf
Source dataset
uspto-grants-1989_08
Patent number
US04859686

Reaction notes

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