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

HRID 726485Notes

Reaction equation

HRID 726485 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-c4e21dec8c5346ef9b9f1079eb18e68f
Source dataset
uspto-grants-1998_01
Patent number
US05709935

Reaction notes

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