Ethanolamine → N-(2-Hydroxyethyl)phthalimide

HRID 1396283Notes

Reaction equation

HRID 1396283 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[C:5]1(=O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[O:6]1>C1(C)C=CC=CC=1>[OH:4][CH2:3][CH2:2][N:1]1[C:5](=[O:6])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:14]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 6811Phthalic Anhydride

Product 1

HCID 77499N-(2-Hydroxyethyl)phthalimideYield 110.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-aminoethanol (41 g, 0.67 mol) and isobenzofuran-1,3-dione (100 g, 0.52 mol) in toluene (300 mL) was refluxed for 12 hours. Volatiles were distilled out to give a residue, which was purified by re-crystallization from chloroform/hexane (v/v, 1:6) to afford 126 as a white solid (110 g, 85%). (ES, m/z) [M+H]+ 192.0; 1H NMR (300 MHz, CDCl3) δ 7.84-7.90 (m, 2H), 7.71-7.77 (m, 2H), 3.87-3.93 (m, 4H), 2.10 (br, 1H).

Workup

  1. distillationVolatiles were distilled out
  2. customto give a residue, which
  3. customwas purified by re-crystallization from chloroform/hexane (v/v, 1:6)

Sources & evidence

ORD record
ord-3334a55d61084e59a9906fb9a9ac2a7b
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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