3-Amino-1,2-propanediol → N-(2,3-Di(acryloyloxy)propyl)hexahydrophthalimide

HRID 1079288Notes

Reaction equation

HRID 1079288 reaction equation
[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[C:7]1(=[O:17])[O:12][C:10](=O)[CH:9]2[CH2:13][CH2:14][CH2:15][CH2:16][CH:8]12>C(O)C>[C:10]([O:6][CH:3]([CH2:4][O:5][C:7](=[O:17])[CH:8]=[CH2:16])[CH2:2][N:1]1[C:7](=[O:17])[CH:8]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:9]2[C:10]1=[O:12])(=[O:12])[CH:9]=[CH2:13]

Participants

4

Reactant 2

HCID 735613-Amino-1,2-propanediolHCID 85689Hexahydrophthalic anhydride

Product 1

HCID 18934212N-(2,3-Di(acryloyloxy)propyl)hexahydrophthalimideYield 109.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 500-ml, two necked flask was equipped with a magnetic stirring bar, heating mantle and condenser. The flask was charged with 46 g of 3-amino-1,2-propanediol (0.50 mol.) and 300 ml of ethanol. Next, 77 g of hexahydrophthalic anhydride (0.50 mol.) was slowly added to the flask after which the reaction was refluxed for 12 hours. The imide formation was confirmed by IR. The ethanol was removed by a rotoevaporator to yield 92 g (81%) of the N-(2,3-dihydroxypropyl)hexahydrophthalimide.

Workup

  1. customA 500-ml, two necked flask was equipped with a magnetic stirring bar
  2. temperatureheating mantle and condenser
  3. temperaturewas refluxed for 12 hours
  4. customThe ethanol was removed by a rotoevaporator

Sources & evidence

ORD record
ord-7d9c2e6e85e0420ca204d7764a901ce8
Source dataset
uspto-grants-1996_12
Patent number
US05580647

Reaction notes

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