Ethanolamine → HCID 86748967, compound

HRID 2399438Notes

Reaction equation

HRID 2399438 reaction equation
[N:1]#N.NC[CH2:5][OH:6].[C:7]1([CH:14]=[CH:13][C:11]([OH:12])=CC=1)[OH:8].ClC(OC=C)=O.[C:21](Cl)(=[O:25])[C:22]([CH3:24])=[CH2:23]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:5](=[O:6])([O:12][CH:11]=[CH:13][CH2:14][CH2:7][O:8][C:21](=[O:25])[C:22]([CH3:24])=[CH2:23])[NH2:1]

Participants

8

Reactant 5

HCID 700EthanolamineHCID 785Hydroquinone2×HCID 947NitrogenHCID 13528Methacryloyl chlorideHCID 78808Vinyl chloroformate

Product 1

HCID 86748967HCID 86748967, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6212ChloroformSolvent4×

Procedure

A 1 liter round bottom flask equipped with a reflux condenser, a mechanical stirrer, a thermometer, a dropping funnel and an efficient N2 blanket, is charged with 30.5 g (0.5 mole) 2-aminoethanol, 100 mg of hydroquinone, 43.6 g of pyridine and 600 ml of chloroform. The contents are cooled down to between 0 and 5 degrees C. Through the dropping funnel, 50.6 g (0.5 mole) of vinyl chloroformate in 100 ml of chloroform is added into the reaction flask at a rate such that the temperature is maintained at between 0 and 5 degrees C. The temperature is allowed to rise to room temperature with constant stirring overnight. The contents are then passed through a silica gel column, dried with magnesium sulfate and then evaporated. The residue is distilled under reduced pressure to recover 2-hydroxyethyl vinyl carbamate. Then using the same equipment, 32.75 g of 2-hydroxyethyl vinyl carbamate (0.25 mole), 50 mg of hydroquinone, 21.8 g of pyridine, and 300 ml of chloroform are added into the reaction flask and cooled to between 0 and 5 degrees C. Through a dropping funnel, 26.5 g (0.25 mole) of methacryloyl chloride in 50 ml of chloroform is added into the reaction flask at a rate such that the temperature is maintained between 0 and 5 degrees C. The temperature is then allowed to rise to room temperature and the contents stirred overnight. The contents are then passed through a silica gel column, dried with magnesium sulfate and evaporated. The final product is recovered by distillation under reduced pressure.

Workup

  1. customA 1 liter round bottom flask equipped with a reflux condenser, a mechanical stirrer
  2. temperatureThe contents are cooled down to between 0 and 5 degrees C
  3. temperatureis maintained at between 0 and 5 degrees C
  4. customto rise to room temperature
  5. dry with materialdried with magnesium sulfate
  6. customevaporated
  7. distillationThe residue is distilled under reduced pressure
  8. customto recover 2-hydroxyethyl vinyl carbamate
  9. additionare added into the reaction flask
  10. temperaturecooled to between 0 and 5 degrees C
  11. temperatureis maintained between 0 and 5 degrees C
  12. customto rise to room temperature
  13. stirringthe contents stirred overnight
  14. dry with materialdried with magnesium sulfate
  15. customevaporated
  16. distillationThe final product is recovered by distillation under reduced pressure

Sources & evidence

ORD record
ord-c45c2c392c254d5f9a90d19515223770
Source dataset
uspto-grants-1995_09
Patent number
US05449729

Reaction notes

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