Trifluoromethanesulfonic acid → HCID 68108727, compound

HRID 385137Notes

Reaction equation

HRID 385137 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[OH:22])[C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:18])(=[O:17])[CH2:9]1)=[O:7])#[N:2].[I:23]N1C(=O)CCC1=O.FC(F)(F)S(O)(=O)=O>ClCCl.CO>[C:1]([C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([I:23])[C:21]=1[OH:22])[C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:18])(=[O:17])[CH2:9]1)=[O:7])#[N:2]

Participants

6

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 68108594HCID 68108594, compound

Product 1

HCID 68108727HCID 68108727, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-(3-cyano-4-hydroxybenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole was dissolved in dichloromethane (27 mL) and methanol (3 mL), and N-iodosuccinimide (1.79 g) and trifluoromethanesulfonic acid (5 droplets) was added to the solution, and then the mixture was stirred at room temperature for 15 hours. The solvent was distilled off under reduced pressure and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was crystallized from n-hexane-ethyl acetate to obtain the title compound (1.30 g) as a colorless crystal.

Workup

  1. distillationThe solvent was distilled off under reduced pressure and water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was crystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-3e3cb413c3c344d78b1b51ac51d240ad
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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