Potassium Iodide → 4-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoro propan-2-yl)-6-methylphenyl]benzamide

HRID 587833Notes

Reaction equation

HRID 587833 reaction equation
Cl[CH2:2][C:3]1[CH:30]=[CH:29][C:6]([C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:12][C:11]=2[CH2:27][CH3:28])=[O:8])=[CH:5][CH:4]=1.[C:31]1(=[O:41])[NH:35][C:34](=[O:36])[C:33]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]12.[K].[I-].[K+]>CN(C)C=O.O>[O:36]=[C:34]1[C:33]2[C:32](=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:31](=[O:41])[N:35]1[CH2:2][C:3]1[CH:30]=[CH:29][C:6]([C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:12][C:11]=2[CH2:27][CH3:28])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 24194345Phthalimide potassium saltHCID 866666154-(Chloromethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]benz amide

Product 1

HCID 866666164-[(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoro propan-2-yl)-6-methylphenyl]benzamideYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-(Chloromethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]benz amide (1.2 g) was dissolved in N,N-dimethylformamide (15 ml). To the solution, potassium phthalimide (0.95 g) and potassium iodide (0.09 g) were added and the mixture was stirred under heating at 60° C. for 2 hours. After adjusting to room temperature, the reaction solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined, washed with water and dried over magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was washed with tert-butyl methyl ether to obtain 4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-methyl]-N-[2-ethyl-4-(1,1,1,2,3,3,3-hepta-fluoropropan-2-yl)-6-methylphenyl]-benzamide (0.85 g, yield 56%).

Workup

  1. customAfter adjusting to room temperature
  2. extractionextracted twice with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtering off the drying agent
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain a crude product
  8. washThe crude product was washed with tert-butyl methyl ether

Sources & evidence

ORD record
ord-c5fd3f00762841939c4fb8c6f8b02468
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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