4-Fluoro-3-(trifluoromethyl)aniline → HCID 58266265, compound

HRID 2039691Notes

Reaction equation

HRID 2039691 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[O-:13][C:14]#[N:15].[K+]>Cl.C(OCC)(=O)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14]([NH2:15])=[O:13])=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

5

Reactant 2

HCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 11378442Potassium cyanate

Product 1

HCID 58266265HCID 58266265, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

2500 mg (13.957 mmol) of 4-fluoro-3-(trifluoromethyl)aniline were dissolved in 15 ml of 1 N hydrochloric acid, and 1132 mg (13.957 mmol) of potassium cyanate were added. The suspension was stirred at room temperature overnight and then diluted with ethyl acetate such that a clear two-phase solution was formed. The organic phase was separated off and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried and the solvent was removed on a rotary evaporator, and the crude product was then chromatographed on silica gel (mobile phase: dichloromethane/methanol 80:1, then 10:1). This gave 2180 mg (70% of theory) of the title compound.

Workup

  1. customwas formed
  2. customThe organic phase was separated off
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. customThe combined organic phases were dried
  5. customthe solvent was removed on a rotary evaporator
  6. customthe crude product was then chromatographed on silica gel (mobile phase

Sources & evidence

ORD record
ord-738191ac94e44975b6e00900ebbaf0dc
Source dataset
uspto-grants-2013_11
Patent number
US08580800B2

Reaction notes

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