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

HRID 1598411Notes

Reaction equation

HRID 1598411 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 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-di(hydroxy)propyl]hexahydrophthalimide.

Workup

  1. customA 500-ml, two necked flask was equipped 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-a2ae3e78b3364107bf9146b5df87b734
Source dataset
uspto-grants-1998_04
Patent number
US05736747

Reaction notes

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