Reaction #674285

Reaction equation

N-ethyl-N-isopropyl-4-aminoaniline hydrochloride

2-(2,4-diaminophenoxy)ethanol dihydrochloride

ammonia

→

2-{4-amino-3-[4-(ethylisopropylamino)phenylimino]-6-iminocyclohexa-1,4-dienyloxy}ethanol hydrochloride

Yield 13.5%

2-{4-amino-3-[4-(ethylisopropylamino)phenylimino]-6-imino-cyclohexan-1,4-dienyloxy}ethanol hydrochloride

Yield 13.5%

Solvents

ethanol

water

Conditions

Workup

1. 1
   OtherThe supernatant is removed
2. 2
   Washthe residual gum is washed with four times of water

Procedure

To a solution of 2.14 g (0.01 mol) of N-ethyl-N-isopropyl-4-aminoaniline hydrochloride and 2.41 g (0.01 mol) of 2-(2,4-diaminophenoxy)ethanol dihydrochloride in 10 ml of water and 10 ml of ethanol, brought to pH 9.5 with 20% aqueous ammonia, are added dropwise 5.7 g of 30% aqueous peroxide hydrogen solution (0.05 mol). After stirring for 6 hours at room temperature, a gum forms. The supernatant is removed and the residual gum is washed with four times of water and then taken up in dichloromethane in order to perform a chromatography (eluent: dichloromethane/methanol 98/2 v/v). 510 mg of 2-{4-amino-3-[4-(ethylisopropylamino)phenylimino]-6-iminocyclohexa-1,4-dienyloxy}ethanol hydrochloride 66 are thus obtained in the form of a black powder.

Source