Trifluoroacetic anhydride → 1,3-Dihydro-7-iodo-3-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoro-methyl)ethyl]phenylimino}-2-benzofuran-1-one

HRID 1373507Notes

Reaction equation

HRID 1373507 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[CH3:30])=[O:12])[C:7]=1[C:8](O)=[O:9].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(OC)(C)(C)C>[I:1][C:2]1[C:7]2[C:8](=[O:9])[O:12][C:11](=[N:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:29])([C:25]([F:26])([F:27])[F:28])[C:21]([F:23])([F:24])[F:22])=[CH:16][C:15]=3[CH3:30])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 120543996-iodo-N-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamic acid

Product 1

HCID 120544001,3-Dihydro-7-iodo-3-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoro-methyl)ethyl]phenylimino}-2-benzofuran-1-oneYield 94.1%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

In methyl t-butyl ether (60 ml) was suspended 5.47 g (10 mmol) of 6-iodo-N-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamic acid, and a solution of 3.15 g (15 mmol) of trifluoroacetic anhydride in methyl t-butyl ether was slowly dropped thereinto. The resulting mixture was stirred at room temperature for 3 hours and then poured into ice water, followed by three runs of extraction with ethyl acetate. The extract solution was washed twice with saturated aqueous sodium hydrogencarbonate solution and then once with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off and the crude crystals thus obtained were washed twice with a solvent (hexane:ethyl acetate=4:1) to obtain 5.0 g (yield 94%) of 1,3-dihydro-7-iodo-3-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoro-methyl)ethyl]phenylimino}-2-benzofuran-1-one.

Workup

  1. extractionfollowed by three runs of extraction with ethyl acetate
  2. washThe extract solution was washed twice with saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialonce with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe crude crystals thus obtained
  6. washwere washed twice with a solvent (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-7a7bb8826e7d4f028cc794067b134793
Source dataset
uspto-grants-2007_01
Patent number
US07161032B2

Reaction notes

Loading…