Methyl iodide → HCID 59398579, compound

HRID 2070048Notes

Reaction equation

HRID 2070048 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][C:8]=2[C:14]([F:17])([F:16])[F:15])=[CH:4][CH:3]=1.[C:20](OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.[H-].[Na+].IC.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH:11][CH3:20])=[CH:9][C:8]=2[C:14]([F:15])([F:16])[F:17])=[CH:18][CH:19]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 90495Di-tert-butyl dicarbonateHCID 17605600HCID 17605600, compound

Product 1

HCID 59398579HCID 59398579, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

4-(4-Fluorophenoxy)-3-trifluoromethyl-aniline (1.0 g, 3.7 mmol) was dissolved in THF (5 mL), and di-t-butyl dicarbonate (965 mg, 4.43 mmol) was added thereto. The resulting mixture was stirred at 80° C. for 3 hours. The reaction solution was concentrated. The residue was dissolved in THF (5 mL), and sodium hydride (258 mg, 5.6 mmol) was added thereto. The resulting mixture was stirred at room temperature for 30 minutes, and then iodomethane (348 μL, 5.6 mmol) was added thereto. The mixture was further stirred overnight, and a saturated ammonium chloride aqueous solution was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and concentrated under reduced pressure. Then, TFA (2 mL) was added to the residue, followed by stirring for 1 hour at room temperature. The reaction solution was concentrated, and a saturated sodium bicarbonate solution was added thereto. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and concentrated under reduced pressure to give a crude product of 4-(4-fluorophenoxy)-3-trifluoromethyl-N-methylaniline.

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionThe residue was dissolved in THF (5 mL)
  3. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  4. waitThe mixture was further stirred overnight
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. concentrationconcentrated under reduced pressure
  8. additionThen, TFA (2 mL) was added to the residue
  9. stirringby stirring for 1 hour at room temperature
  10. concentrationThe reaction solution was concentrated
  11. additiona saturated sodium bicarbonate solution was added
  12. extractionThe resulting mixture was extracted with ethyl acetate
  13. washThe organic layer was washed with saturated brine
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92f84868da914405be96c7b94843a15e
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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