Trifluoroacetic acid → HCID 22921587, compound

HRID 2258612Notes

Reaction equation

HRID 2258612 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:8]=1)[NH2:7].[F:9][C:10]([F:15])([F:14])[C:11](O)=O>>[CH2:6]([N:7]1[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:8][C:6]=2[N:7]=[C:11]1[C:10]([F:15])([F:14])[F:9])[C:5]#[CH:4]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 97423-Fluoroaniline

Product 1

HCID 22921587HCID 22921587, compound

Procedure

Under a nitrogen atmosphere, a stirred solution of 5.0 grams (0.030 mole) of 2-propyn-1-ylamino)-5-fluoroaniline in 70 mL of trifluoroacetic acid was heated at reflux for 1.5 hours. The reaction mixture was then cooled to ambient temperature and poured into ice water. The mixture was extracted thoroughly with portions of diethyl ether. The combined extracts were washed with an aqueous solution saturated with sodium bicarbonate and then dried with magnesium sulfate. The mixture was filtered, and the filtrate concentrated under reduced pressure to a residual oil. The oil was triturated with cold water, and the resultant solid was collected by filtration. The solid was dried, yielding 5.0 grams of 1-(2-propyn-1-yl)-2-trifluoromethyl-5-fluorobenzimidazole. The NMR spectrum was consistent with the proposed structure. The reaction was repeated.

Workup

  1. temperatureat reflux for 1.5 hours
  2. extractionThe mixture was extracted thoroughly with portions of diethyl ether
  3. washThe combined extracts were washed with an aqueous solution saturated with sodium bicarbonate
  4. dry with materialdried with magnesium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated under reduced pressure to a residual oil
  7. customThe oil was triturated with cold water
  8. filtrationthe resultant solid was collected by filtration
  9. customThe solid was dried

Sources & evidence

ORD record
ord-fd6e153123c94b58bbe7e8d8ae4afc04
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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