3-(4-Cyanophenyl)propyl methanesulfonate → 4-(3-Phthalimidopropyl)benzonitrile

HRID 485279Notes

Reaction equation

HRID 485279 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].S(O[CH2:18][CH2:19][CH2:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)(C)(=O)=O>CN(C=O)C>[C:1]1(=[O:11])[N:5]([CH2:18][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=2)[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

4

Reactant 2

HCID 219936463-(4-Cyanophenyl)propyl methanesulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 134213034-(3-Phthalimidopropyl)benzonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

To 100 ml of DMF suspension of 21.1 g (0.114 mol) of potassium phthalimide was added 50 ml of DMF solution of 13.6 g (57 mmols) of crude 4-(3-mesyloxypropyl)benzonitrile. The reaction mixture was stirred at 90° C. for 3 hours, then cooled to room temperature and poured into 200 ml of ice-water, followed by extraction with ether-benzene (1:1). The organic layer was dried over Na2SO4 and concentrated, giving 14.0 g (yield 85%) of 4-(3-phthalimidopropyl)benzonitrile.

Workup

  1. temperaturecooled to room temperature
  2. extractionfollowed by extraction with ether-benzene (1:1)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-263442db364047469babe0d857cfd484
Source dataset
uspto-grants-1985_08
Patent number
US04536391

Reaction notes

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