Ethanolamine → HCID 178438304, compound

HRID 568581Notes

Reaction equation

HRID 568581 reaction equation
[CH2:1]([C:4]12[CH2:10][CH:7]([CH:8]=[CH:9]1)[CH:6]1[C:11]([O:13][C:14](=[O:15])[CH:5]21)=[O:12])[CH:2]=[CH2:3].[CH2:16]([CH2:18][NH2:19])[OH:17]>>[OH:17][CH2:16][CH2:18][N:19]=[C:14]([CH:5]1[CH:6]([C:11]([OH:13])=[O:12])[CH:7]2[CH2:10][C:4]1([CH2:1][CH:2]=[CH2:3])[CH:9]=[CH:8]2)[OH:15]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 54206110Allylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride

Product 1

HCID 178438304HCID 178438304, compound

Procedure

760 g of allylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (isomeric mixture) are placed into the reaction vessel, and 227.55 g of monoethanolamine are added dropwise with stirring. The mixture is refluxed for 2 hours, and water and some excess monoethanolamine are distilled off until a temperature of 175° C. is reached. The pressure is then decreased to 2670 Pa. The temperature is lowered to 100° C. and the product is rectified at 4.9 Pa. At between 170° and 174° C., there distil over 712.4 g (77.3% of theory) of a pale yellow oil having the following characteristic values:

Workup

  1. additionare added dropwise
  2. temperatureThe mixture is refluxed for 2 hours
  3. distillationwater and some excess monoethanolamine are distilled off until a temperature of 175° C.
  4. customis lowered to 100° C.
  5. customAt between 170° and 174° C., there distil over 712.4 g (77.3% of theory) of a pale yellow oil

Sources & evidence

ORD record
ord-9281f3792cc344d8bf670ed9d749689a
Source dataset
uspto-grants-1988_03
Patent number
US04728742

Reaction notes

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