Water → HCID 10679822, compound

HRID 710953Notes

Reaction equation

HRID 710953 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[C:13]([O-])(=[O:15])[CH3:14].[Na+].BrCCO.O>CS(C)=O>[OH:15][CH2:13][CH2:14][O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 10665N-HydroxyphthalimideHCID 108982-BromoethanolHCID 517045Sodium Acetate

Product 1

HCID 10679822HCID 10679822, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-hydroxyphthalimide (2.20 g, 13.5 mmol) and sodium acetate (3.30 g) in dimethylsulfoxide (40 mL) was added 2-bromoethanol (2.88 mL) under an argon atmosphere at room temperature. The reaction mixture was stirred at 70° C. for 5 hours, followed by cooling to room temperature, adding water (40 mL), and extracting with methylene chloride. The resulting organic layer was washed with water, 2.5M hydrochloric acid, and saturated brine. The washed organic layer was dried over magnesium sulfate, the residue resulting from distilling off the solvent under reduced pressure was recrystallized with ethanol and water to afford 1.86 g of the title compound (yield 66%).

Workup

  1. temperatureby cooling to room temperature
  2. extractionextracting with methylene chloride
  3. washThe resulting organic layer was washed with water, 2.5M hydrochloric acid, and saturated brine
  4. dry with materialThe washed organic layer was dried over magnesium sulfate
  5. customthe residue resulting
  6. distillationfrom distilling off the solvent under reduced pressure
  7. customwas recrystallized with ethanol and water

Sources & evidence

ORD record
ord-559c5cc84daa4e088a8d6db5a77b2168
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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