Iodine → HCID 67100580, compound

HRID 2079916Notes

Reaction equation

HRID 2079916 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[NH2:14])#[C:2]CC.FC(F)(F)C(O[C:20](=O)[C:21](F)(F)F)=O.C(=O)([O-])[O-].[K+].[K+].[I:34]I>C1COCC1.O.C(OCC)(=O)C>[CH2:20]([N:14]1[C:6]2[C:5](=[CH:10][CH:9]=[C:8]([N+:11]([O-:13])=[O:12])[CH:7]=2)[C:1]([I:34])=[CH:2]1)[CH3:21]

Participants

8

Reactant 4

HCID 807IodineHCID 9845Trifluoroacetic anhydrideHCID 11430Potassium CarbonateHCID 67101312HCID 67101312, compound

Product 1

HCID 67100580HCID 67100580, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add to a solution of 2-but-ynyl-5-nitro-phenylamine (2.98 g, 15.68 mmol) in anhydrous THF (100 mL) 2,6-di-t-butyl-4-methylpyridine followed by trifluoroacetic anhydride (2.7 mL, 19.61 mmol) and stir at room temperature for 18 hours. Quench the reaction with 1N HCl and add ethyl acetate. Extract the organic layer 2×1N HCl, 1× brine. Dry the organic layer over sodium sulfate, concentrate in vacuo, and redissolve in anhydrous acetonitrile (150 mL). Add to the solution potassium carbonate (6.49 g, 47.04 mmol) and cool to 0° C. Add iodine (11.94 g, 47.04 mmol) and stir at 0° C. for 30 min. Quench the reaction with 1M sodium thiosulfate (100 mL) and add water (250 mL). Stir the mixture 30 min., then filter and rinse with water to afford 3.94 g (80%) of the title compound.

Workup

  1. customQuench
  2. customthe reaction with 1N HCl
  3. extractionExtract the organic layer 2×1N HCl, 1× brine
  4. dry with materialDry the organic layer over sodium sulfate
  5. concentrationconcentrate in vacuo
  6. dissolutionredissolve in anhydrous acetonitrile (150 mL)
  7. temperaturecool to 0° C
  8. customQuench
  9. customthe reaction with 1M sodium thiosulfate (100 mL)
  10. stirringStir the mixture 30 min.
  11. filtrationfilter
  12. washrinse with water

Sources & evidence

ORD record
ord-6e03ec37f0494961afa91c3b22357bef
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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