Dimethylformamide → N-(Prop-2-ynyloxy)phthalimide

HRID 1380951Notes

Reaction equation

HRID 1380951 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].[CH2:13](Br)[C:14]#[CH:15].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(O)C>[CH2:15]([O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])[C:14]#[CH:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 10665N-HydroxyphthalimideHCID 11430Potassium Carbonate

Product 1

HCID 78357N-(Prop-2-ynyloxy)phthalimideYield 63.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 163.1 grams (1.00 mole) of N-hydroxyphthalimide, 448.0 grams (3.74 moles) of 2-propynyl bromide, 72.0 grams (0.52 mole) of potassium carbonate and 60.0 grams (0.82 mole) of dimethylformamide was heated under reflux for 16 hours. The reaction mixture containing a hardened solid was cooled. The solid was broken up by the addition of ethanol and stirring. The solid was collected by filtration and washed with additional ethanol, then with water until the washings were free of bromide ion when tested with silver ion. The solid was dried in a vacuum desiccator then recrystallized from hot ethanol to give 127.3 grams of N-2-propynoxyphthalimide; mp 146°-148.5°.

Workup

  1. temperatureunder reflux for 16 hours
  2. additionThe reaction mixture containing a hardened solid
  3. temperaturewas cooled
  4. filtrationThe solid was collected by filtration
  5. washwashed with additional ethanol
  6. customThe solid was dried in a vacuum desiccator
  7. customthen recrystallized from hot ethanol

Sources & evidence

ORD record
ord-c4dee3c32f1f491e850b1fb545b820c0
Source dataset
uspto-grants-1986_04
Patent number
US04584318

Reaction notes

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