Diphenyl Ether → HCID 178516461, compound

HRID 418451Notes

Reaction equation

HRID 418451 reaction equation
[F:1][CH:2]([F:11])[O:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6].[C:12]1([O:18]C2C=CC=CC=2)C=CC=[CH:14][CH:13]=1.CCCC(C)C>C(#N)C>[F:1][CH:2]([F:11])[O:3][C:4]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:5]=1[N:6]=[CH:14][CH:13]=[C:12]2[OH:18]

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 78922-MethylpentaneHCID 9346202-(Difluoromethoxy)aniline

Product 1

HCID 178516461HCID 178516461, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-difluoromethoxyaniline (7.63 g) and the product from step a) were stirred in acetonitrile (100 ml) overnight. The solvent was removed by evaporation and the solid triturated with 4:1 isohexane/diethyl ether (200 ml) before filtering to give a light green solid. The solid was added portionwise to refluxing diphenylether (120 ml) and continued heating for a further 10 minutes before cooling. The solution was poured into isohexane (600 ml) and the solid filtered off to give the title compound (12.0 g).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe solid triturated with 4:1 isohexane/diethyl ether (200 ml)
  3. filtrationbefore filtering
  4. customto give a light green solid
  5. additionThe solid was added portionwise
  6. temperaturecontinued heating for a further 10 minutes
  7. temperaturebefore cooling
  8. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-4cc948c9ffb34d069ef25ec8ec3f8d63
Source dataset
uspto-grants-2012_01
Patent number
US08093278B2

Reaction notes

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