Reaction #87289

ord-4cf052ea8c254f09bf3992e6e71354c9

Reaction equation

CCN(c1ccc(N)cc1)C(C)C.Cl
N-ethyl-N-isopropyl-4-aminoaniline hydrochloride
CCO
ethanol
N
ammonia
O=S(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+]
ammonium persulfate
Cc1cc(O)cc(O)c1
orcinol
→
CCN(c1ccc(N=C2C(O)=CC(=O)C(Nc3ccc(N(CC)C(C)C)cc3)=C2C)cc1)C(C)C
2-[4-(ethylisopropylamino)-phenylamino]-4-[4-(ethylisopropylamino)phenylimino]-5-hydroxy-3-methylcyclohexa-2,5-dienone

Reactants

CCN(c1ccc(N)cc1)C(C)C.Cl
N-ethyl-N-isopropyl-4-aminoaniline hydrochloride
CCO
ethanol
N
ammonia
O=S(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+]
ammonium persulfate
Cc1cc(O)cc(O)c1
orcinol

Reagents

None

Solvents

O
water
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONis added dropwise
  2. 2
    workup.ADDITIONThe temperature is held below 30° C. during the addition
  3. 3
    workup.ADDITIONAt the end of the addition
  4. 4
    Otherthe precipitate formed
  5. 5
    Filtrationis filtered
  6. 6
    Washwashed with water

Procedure

To a solution of 0.002 mol (429 mg) of N-ethyl-N-isopropyl-4-aminoaniline hydrochloride and 0.001 mol (124 mg) of orcinol in 2 ml of water and 6 ml of ethanol brought to a pH of 9.5 with a solution of 20% aqueous ammonia, 0.002 mol (456 mg) of ammonium persulfate dissolved in 1 ml of water is added dropwise. The temperature is held below 30° C. during the addition. At the end of the addition, the precipitate formed is filtered and washed with water.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09439844B2uspto-grants-2016_09