Diglycolamine → N-(2-hydroxyethoxyethyl)hexahydrophthalimide

HRID 1079286Notes

Reaction equation

HRID 1079286 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].[C:8]1(=O)[O:13][C:11](=[O:12])[CH:10]2[CH2:14][CH2:15][CH2:16][CH2:17][CH:9]12>C(O)C>[OH:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][N:1]1[C:11](=[O:12])[CH:10]2[CH2:14][CH2:15][CH2:16][CH2:17][CH:9]2[C:8]1=[O:13]

Participants

4

Reactant 2

HCID 13578DiglycolamineHCID 85689Hexahydrophthalic anhydride

Product 1

HCID 55023972N-(2-hydroxyethoxyethyl)hexahydrophthalimideYield 96%

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 51 g of 2-(aminoethoxy)ethanol (0.49 mol.) and 250 ml of ethanol. Next, 75 g of hexahydrophthalic anhydride (0.49 mol.) was slowly added to the flask. After the addition was complete the reaction was refluxed for 12 hours. The IR spectrum indicated the reaction was complete. The ethanol was removed with a rotoevaporator to yield 113 g (96%) of N-(2-hydroxyethoxyethyl)hexahydrophthalimide.

Workup

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

Sources & evidence

ORD record
ord-d7a5f42e0d1b4f279c8a6aa15e4901d2
Source dataset
uspto-grants-1996_12
Patent number
US05580647

Reaction notes

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