Phthalimide → HCID 17391118, compound

HRID 2174574Notes

Reaction equation

HRID 2174574 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+].[Br:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Br>CN(C=O)C.O>[Br:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]

Participants

6

Reactant 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 699793-Bromobenzyl bromide

Product 1

HCID 17391118HCID 17391118, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of phthalimide (0.64 g, 4.4 mmol) in DMF (10 ml) was added K2CO3 (1.65 g, 12.00 mmol), followed by 3-bromobenzyl bromide (1 g, 4.0 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 cool water (50 ml), resultant solid was filtered and dried under vacuum for 3 h to get the desired compound as a white solid (1.2 g, 95%). 1H NMR (400 MHz, DMSO-d6) δ 7.92-7.84 (m, 4H), 7.54 (s, 1H), 7.50-7.45 (m, 1H), 7.33-7.26 (m, 2H), 4.77 (s, 2H).

Workup

  1. stirringAfter 16 h of stirring
  2. filtrationresultant solid was filtered
  3. customdried under vacuum for 3 h

Sources & evidence

ORD record
ord-b8ed401ce84d40d1a2e2529f1330d4f6
Source dataset
uspto-grants-2015_06
Patent number
US09062002B2

Reaction notes

Loading…