2-(N-ethyl-p-nitrosoanilino)ethanol → 2-[4-[(2-amino-5-ethoxy-4-iminocyclohexa-2,5-dien-1-ylidene)amino]-N-ethylanilino]ethanol;hydrochloride

HRID 587102Notes

Reaction equation

HRID 587102 reaction equation
[ClH:1].Cl.[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=1[NH2:15])[CH2:4]CC.[CH2:16]([N:18]([C:22]1[CH:27]=[CH:26][C:25]([N:28]=O)=[CH:24][CH:23]=1)[CH2:19][CH2:20][OH:21])[CH3:17]>[OH-].[Na+].O>[ClH:1].[NH2:14][C:11]1[C:12](=[N:28][C:25]2[CH:24]=[CH:23][C:22]([N:18]([CH2:16][CH3:17])[CH2:19][CH2:20][OH:21])=[CH:27][CH:26]=2)[CH:13]=[C:8]([O:7][CH2:3][CH3:4])[C:9](=[NH:15])[CH:10]=1

Participants

5

Reactant 2

HCID 672812-(N-ethyl-p-nitrosoanilino)ethanolHCID 1536941,3-Benzenediamine, 4-butoxy-, dihydrochloride

Product 1

HCID 1406628342-[4-[(2-amino-5-ethoxy-4-iminocyclohexa-2,5-dien-1-ylidene)amino]-N-ethylanilino]ethanol;hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-butoxybenzene-1,3-diamine dihydrochloride in 4.2 ml of 0.25N sodium hydroxide is added to a solution of 2-[ethyl(4-nitrosophenyl)amino]ethanol in 4.2 ml of water at 50° C. After 3 hours at 50° C., the supernatant is removed and the residual gum is washed with water and then taken up in isopropyl ether. The solid formed is filtered off and dried. 360 mg of 2-{[4-(2-amino-5-ethoxy-4-imino cyclohexa-2,5-dienylideneamino)phenyl]-ethylamino}ethanol hydrochloride 65 are thus obtained in the form of a black powder.

Workup

  1. customthe supernatant is removed
  2. washthe residual gum is washed with water
  3. customThe solid formed
  4. filtrationis filtered off
  5. customdried

Sources & evidence

ORD record
ord-22098969bbba4ea287b484e5944a52f6
Source dataset
uspto-grants-2016_01
Patent number
US09226883B2

Reaction notes

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