Hydrochloric Acid → N-(2,2,2-trifluoroethoxy)phthalimide

HRID 644125Notes

Reaction equation

HRID 644125 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.O[N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33].C(N(CC)C(C)C)(C)C.Cl>ClCCl.N1C=CC=CC=1>[F:1][C:2]([F:6])([F:5])[CH2:3][O:4][N:23]1[C:24](=[O:33])[C:25]2=[CH:32][CH:31]=[CH:30][CH:29]=[C:26]2[C:27]1=[O:28]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 10665N-HydroxyphthalimideHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531Diisopropylethylamine

Product 1

HCID 10562310N-(2,2,2-trifluoroethoxy)phthalimide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent3×

Procedure

A dichloromethane (21 mL) solution of 3.9 mL of 2,2,2-trifluoroethanol and 4.3 mL of pyridine was added dropwise to a dichloromethane (83 mL) solution of 9.0 mL of trifluoromethanesulfonic anhydride under cooling with ice over a period of 25 minutes. Thereto was dropwise added a dichloromethane (60 mL) solution of 8.50 g of N-hydroxyphthalimide and 18.5 mL of N,N-diisopropylethylamine at the same temperature over a period of 45 minutes, which was then stirred for 22 hours. To the reaction mixture was added 100 mL of 1 mol/L hydrochloric acid. The organic layer was separated, washed sequentially with 1 mol/L hydrochloric acid and a saturated sodium chloride aqueous solution, and then dried with anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; hexane:ethyl acetate=3:1) and washed with hexane to provide 4.43 g of N-(2,2,2-trifluoroethoxy)phthalimide as white solid form.

Workup

  1. temperatureunder cooling with ice over a period of 25 minutes
  2. customThe organic layer was separated
  3. washwashed sequentially with 1 mol/L hydrochloric acid
  4. dry with materiala saturated sodium chloride aqueous solution, and then dried with anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe resultant residue was purified
  7. washwashed with hexane

Sources & evidence

ORD record
ord-d519863063864a0ebe5d22a3a1ad75bd
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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