Trifluoromethanesulfonate → Phthalimide

HRID 921478Notes

Reaction equation

HRID 921478 reaction equation
[O-]S(C(F)(F)F)(=O)=O.[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.[K]>CN(C)C=O.[Cl-].[Na+].O>[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12

Participants

5

Reactant 2

HCID 2758875TrifluoromethanesulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of compound 30 (3.0 g, 5.7 mmol) in dry N,N-dimethylformamide (300 mL), potassium phthalimide (2.53 g, 13.7 mmol) was added under nitrogen atmosphere. The mixture was stirred at 85° C. overnight. The reaction mixture was cooled down to room temperature and 300 mL of brine was added. The product precipitated as a white solid and was collected by filtration (2.6 g, 89%). Decomp. temp and mp. 260.5-262° C. 1H NMR (400 MHz, CDCl3): δ=7.93 (q, 3JH,H=2.8 Hz, Ar, 4H), 7.78 (q, 3JH,H=2.8 Hz, Ar, 4H), 4.38 (t, 3JH,F=15.6 Hz, 4H, NCH2CF2). 13C NMR (100 MHz, CDCl3): δ=166.8 (s, Ar), 134.5 (s, Ar), 131.8 (s, Ar), 123.9 (s, Ar), 37.6 (t, 3JC,F=25.1 Hz, NCH2). 19F NMR (376 MHz, CDCl3): δ=−123.5-−123.6 (m, 4F, CF2CF2CH2), −116.4-−(116.6) (m, 4F, CF2CH2N). Anal. Calc'd for C13H13O4N: C, 50.78; H, 2.32; N, 5.38. Found: C, 50.73; H, 2.03; 5.05. FT-IR (cm−1, in CHCl3): v=3019, 2400, 1522, 1424, 1216, 930, 759. This data is consistent with a previously-reported compound.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. customThe product precipitated as a white solid
  3. filtrationwas collected by filtration (2.6 g, 89%)

Sources & evidence

ORD record
ord-adc79d25f98344d59b7863c19afd22a6
Source dataset
uspto-grants-2016_03
Patent number
US09273184B1

Reaction notes

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