Ethanol → N-(5-Hexynyl)phthalimide

HRID 569553Notes

Reaction equation

HRID 569553 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].Cl[CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[CH:19].C(O)C>CN(C)C=O>[CH2:19]([N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6])[CH2:18][CH2:17][CH2:16][C:15]#[CH:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 2720016-Chloro-1-hexyneHCID 24194345Phthalimide potassium salt

Product 1

HCID 3346053N-(5-Hexynyl)phthalimideYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To potassium phthalimide (37.5 g) in dimethylformamide (400 ml) at 100° C. was added dropwise 1-chloro-5-hexyne (23.67 g) in dimethylformamide (100 ml). The reaction mixture was stirred at 100° C. for a further hour, cooled and stirred at room temperature overnight. The mixture was poured on to ice/water to give an oil, which on trituration gave as a white solid N-5-hexynyl phthalimide (18.35 g), m.p. 74°-6° C. (recrystallisation from ethanol).

Workup

  1. temperaturecooled
  2. stirringstirred at room temperature overnight
  3. customto give an oil, which on trituration

Sources & evidence

ORD record
ord-aee4997577d0402ebbb350151634c4da
Source dataset
uspto-grants-1988_03
Patent number
US04732980

Reaction notes

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