Ammonia → 2-[4-Amino-3-[4-[ethyl(propan-2-yl)amino]phenyl]imino-6-iminocyclohexa-1,4-dien-1-yl]oxyethanol;hydrochloride

HRID 587103Notes

Reaction equation

HRID 587103 reaction equation
[ClH:1].[CH2:2]([N:4]([CH:12]([CH3:14])[CH3:13])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:3].Cl.Cl.[NH2:17][C:18]1[CH:27]=[C:26]([NH2:28])[CH:25]=[CH:24][C:19]=1[O:20][CH2:21][CH2:22][OH:23].N>O.C(O)C>[ClH:1].[NH2:28][C:26]1[C:25](=[N:11][C:8]2[CH:9]=[CH:10][C:5]([N:4]([CH2:2][CH3:3])[CH:12]([CH3:13])[CH3:14])=[CH:6][CH:7]=2)[CH:24]=[C:19]([O:20][CH2:21][CH2:22][OH:23])[C:18](=[NH:17])[CH:27]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 479322-(2',4'-Diaminophenoxy)ethanol dihydrochlorideHCID 16211123N-Ethyl-N-isopropyl-p-phenylenediamine hydrochloride

Product 1

HCID 1406628352-[4-Amino-3-[4-[ethyl(propan-2-yl)amino]phenyl]imino-6-iminocyclohexa-1,4-dien-1-yl]oxyethanol;hydrochlorideYield 13.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

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.

Workup

  1. customThe supernatant is removed
  2. washthe residual gum is washed with four times of water

Sources & evidence

ORD record
ord-a24c5e1123f1461692081a9448e9dce6
Source dataset
uspto-grants-2016_01
Patent number
US09226883B2

Reaction notes

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