Ethanolamine → N-(2-hydroxyethyl) tetrabromophthalimide

HRID 1415108Notes

Reaction equation

HRID 1415108 reaction equation
[Br:1][C:2]1[C:3]([Br:15])=[C:4]([Br:14])[C:5]([Br:13])=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]=12.[CH2:16]([CH2:18][NH2:19])[OH:17].O>C1(C)C(C)=CC=CC=1>[OH:17][CH2:16][CH2:18][N:19]1[C:8](=[O:10])[C:7]2=[C:2]([Br:1])[C:3]([Br:15])=[C:4]([Br:14])[C:5]([Br:13])=[C:6]2[C:11]1=[O:12]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 962Water2×HCID 12443Tetrabromophthalic anhydride

Product 1

HCID 19812166N-(2-hydroxyethyl) tetrabromophthalimide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a suspension of 464 gm (1 mole) of tetrabromophthalic anhydride in 1.2 liters of xylene was added 61 gm (1 mole) of ethanolamine. The solution was heated and refluxed with a Dean-Stark water separator until the theoretical amount of water separated. The mixture was cooled, diluted with hexane, and filtered. The resulting 413 gm of an off-white solid was washed with hexane and dried at 100° C. This material is used as is for subsequent reactions without further purification.

Workup

  1. temperatureThe solution was heated
  2. customseparated
  3. temperatureThe mixture was cooled
  4. additiondiluted with hexane
  5. filtrationfiltered
  6. washThe resulting 413 gm of an off-white solid was washed with hexane
  7. customdried at 100° C
  8. customas is for subsequent reactions without further purification

Sources & evidence

ORD record
ord-28ab706dc0ad4f999b63ddaea580c57f
Source dataset
uspto-grants-1977_01
Patent number
US04003862

Reaction notes

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