Benzenamine, 3,5-bis(trifluoromethyl)- → HCID 86658339, compound

HRID 2198035Notes

Reaction equation

HRID 2198035 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].C[O:17][CH:18]1[CH:22]([CH:23]=O)[CH2:21][CH:20](OC)O1>C(O)(=O)C>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([N:6]2[CH:20]=[CH:21][C:22]([CH:18]=[O:17])=[CH:23]2)[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

4

Reactant 2

HCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde

Product 1

HCID 86658339HCID 86658339, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3,5-bis(trifluoromethyl)aniline (3.58 g) and 2,5-dimethoxy-3-tetrahydrofurancarbaldehyde (2.50 g) in acetic acid (16 mL) was stirred at 90° C. for 30 min. After cooling to room temperature, the reaction solution was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and saturated sodium hydrogencarbonate solution. The ethyl acetate layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 70:30) to give the title compound (2.44 g, yield 51%) as a pale-yellow solid.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and saturated sodium hydrogencarbonate solution
  3. washThe ethyl acetate layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 70:30)

Sources & evidence

ORD record
ord-3131e3e7d0af4b71a067d44555a1fc27
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

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