Hydrochloric Acid → HCID 18354092, compound

HRID 1603982Notes

Reaction equation

HRID 1603982 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([N+:25]([O-])=O)[CH:16]=2)[CH:9]=1)([O-])=O.[H][H].Cl>C(O)(C)C.[Pd]>[NH2:25][C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=1)[O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:7][C:6]2[CH:28]=[C:29]([C:31]([F:32])([F:34])[F:33])[CH:30]=[C:4]([NH2:1])[CH:5]=2)[CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 18691940HCID 18691940, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18354092HCID 18354092, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent2×

Procedure

Into a reducing device equipped with a thermometer, a reflux condenser and an agitator were charged 72 g of 1,3-bis(3-nitro-5-trifluoromethylphenoxy)benzene (0.147 mol), 500 mL of isopropyl alcohol and 7.2 g of 5%-Pd/C (50% of water content), and the mixture was reacted at 50° C. for 5 hours in an atmosphere of hydrogen. At the end of the reaction, the catalyst was filtered out, the filtrate was condensed under a reduced pressure and the residue was dissolved in 200 g of isopropanol and 400 g of 36% HCl was added to the solution to precipitate the desired hydrochloride. The hydrochloride was suspended in 150 g of water and 200 g of 1, 2-dichloroethane (EDC), the mixture was neutralized with 28% ammonium hydroxide aq. and separated, and the EDC layer was washed with water and evaporated to give 1,3-bis(3-amino-5-trifluoromethylphenoxy)benzene as a brown viscous liquid; Yield: 33.8 g (53.7%).

Workup

  1. customInto a reducing device equipped with a thermometer, a reflux condenser
  2. customAt the end of the reaction
  3. filtrationthe catalyst was filtered out
  4. customcondensed under a reduced pressure
  5. customto precipitate the desired hydrochloride
  6. customseparated
  7. washthe EDC layer was washed with water
  8. customevaporated

Sources & evidence

ORD record
ord-cee7791629ba4cf6bce7b56d0fc164da
Source dataset
uspto-grants-1999_11
Patent number
US05990261

Reaction notes

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