Phthalimide → HCID 17755957, compound

HRID 2174573Notes

Reaction equation

HRID 2174573 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.C([O-])([O-])=O.[K+].[K+].[I:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1>CN(C=O)C.O>[I:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 9542584-Iodobenzyl bromide

Product 1

HCID 17755957HCID 17755957, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of phthalimide (0.6 g, 4.0 mmol) in DMF (5 ml) was added K2CO3 (2.25 g, 16.00 mmol), followed by 4-iodobenzyl bromide (1.33 g, 4.4 mmol) at 0° C. and the reaction mixture was stirred at 20-35° C. for 16 h. The progress of the reaction was monitored by TLC. After 16 h of stirring, the mixture was diluted with water (50 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with brine (50 ml), followed by drying over anhydrous Na2SO4 and filtering. The filtrate was rotary evaporated to get residue which was washed with diethyl ether to get the desired compound as a white solid (700 mg, 50%). 1H NMR (400 MHz, DMSO-d6) δ 7.91-7.84 (m, 4H), 7.70-7.66 (m, 2H), 7.12 (d, J=8.3 Hz, 2H), 4.72 (s, 2H).

Workup

  1. stirringAfter 16 h of stirring
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. washThe combined organic layers were washed with brine (50 ml)
  4. dry with materialby drying over anhydrous Na2SO4
  5. filtrationfiltering
  6. customThe filtrate was rotary evaporated
  7. customto get residue which
  8. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-5af6461493f249d5bf04595f0752d8c5
Source dataset
uspto-grants-2015_06
Patent number
US09062002B2

Reaction notes

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