Dimethylformamide → N-(2-Hydroxyethyl)phthalimide

HRID 964724Notes

Reaction equation

HRID 964724 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH:14]([OH:16])[CH3:15].CN(C)C=O>>[C:1]1(=[O:11])[N:5]([CH2:15][CH2:14][OH:16])[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 14202443Ethanol, 1-bromo-HCID 24194345Phthalimide potassium salt

Product 1

HCID 77499N-(2-Hydroxyethyl)phthalimideYield 44.12%

Conditions

Temperature
70 °C

Procedure

Potassium phthalimide 2 (2.7 g, 14.6 mmol) was added to a solution of bromoethanol 1 in N,N-dimethylformamide (12 mL, 14.1 mmol). After stirring for 12 h at 70° C., the mixture was concentrated and then diluted with dichloromethane (100 mL). After removal of solids by filtration, the organic layer was washed with water, dried, and concentrated. The concentrate was purified by flash column chromatography (3:2 to 2:3 hexane-ethyl acetate) to give compound 3 as a white solid (1.19 g, 44.12%) having a RF of 0.22 (3:2 hexane-ethyl acetate). See FIG. 2.

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with dichloromethane (100 mL)
  3. customAfter removal of solids
  4. filtrationby filtration
  5. washthe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography (3:2 to 2:3 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4ae828ec6cc342fab571422535917093
Source dataset
uspto-grants-1998_06
Patent number
US05770716

Reaction notes

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