Ammonia → 4-Butoxy-6-[4-(ethylisopropylamino)phenylamino]-3-iminocyclohexa-1,4-dienylamine hydrochloride

HRID 587099Notes

Reaction equation

HRID 587099 reaction equation
[ClH:1].[CH3:2][N:3]([CH:11]([CH3:13])[CH3:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.Cl.Cl.[CH2:16]([O:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=1[NH2:28])[CH2:17][CH2:18][CH3:19].N.OO.[CH2:32](O)C>O>[ClH:1].[CH2:16]([O:20][C:21]1[C:22](=[NH:28])[CH:23]=[C:24]([NH2:27])[CH:25]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([N:3]([CH2:2][CH3:32])[CH:11]([CH3:13])[CH3:12])=[CH:5][CH:6]=2)[CH:26]=1)[CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 702EthanolHCID 784Hydrogen PeroxideHCID 1536941,3-Benzenediamine, 4-butoxy-, dihydrochlorideHCID 89619299N-methyl-N-isopropyl-4-aminoaniline hydrochloride

Product 1

HCID 896198154-Butoxy-6-[4-(ethylisopropylamino)phenylamino]-3-iminocyclohexa-1,4-dienylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.003 mol of N-methyl-N-isopropyl-4-aminoaniline hydrochloride and 0.003 mol of 4-butoxybenzene-1,3-diamine dihydrochloride in 2 ml of water and 6 ml of ethanol, brought to pH 9.5 with 20% aqueous ammonia solution, are added 10.2 ml of 20-V 6% aqueous hydrogen peroxide solution; after stirring for 24 hours at room temperature, a gum forms. The supernatant is removed and the gum is washed with three times 50 ml of water, 4 ml of ethyl acetate and then with isopropyl ether. After drying, 260 mg of 4-butoxy-6-[4-(ethylisopropylamino)phenylamino]-3-iminocyclohexa-1,4-dienylamine hydrochloride 1 are obtained in the form of a black powder.

Workup

  1. customThe supernatant is removed
  2. washthe gum is washed with three times 50 ml of water, 4 ml of ethyl acetate
  3. customAfter drying

Sources & evidence

ORD record
ord-e6f2cbdaf0d542178d51870d0b63011a
Source dataset
uspto-grants-2016_01
Patent number
US09226883B2

Reaction notes

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