2-Ethylaniline → N,N'-Bis(2-ethylphenyl)acetamidine

HRID 925030Notes

Reaction equation

HRID 925030 reaction equation
Cl[C:2](=[N:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH3:12])[CH3:3].[CH2:13]([C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1[NH2:17])[CH3:14].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[NH:4][C:2](=[N:17][C:16]1[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=1[CH2:13][CH3:14])[CH3:3])[CH3:12]

Participants

5

Reactant 3

HCID 113572-EthylanilineHCID 14798Sodium HydroxideHCID 87345395HCID 87345395, compound

Product 1

HCID 15379807N,N'-Bis(2-ethylphenyl)acetamidineYield 82.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(1-chloroethylidene)-2-ethylbenzenamine (HS Imine I) (1.82 g, 10 mmol) was dissolved in 50 mL of toluene. 2-ethylaniline (1.24 mL, 10 mmol) was added dropwise at room temperature, resulting in a light pink solution, which was refluxed overnight. Toluene was removed under vacuum. Sodium hydroxide (100 mL of 0.10 M solution, 10 mmol) was added and the solution was stirred for 1 hour. The solid that deposited was extracted into 150 mL of diethylether. The ether layer was dried with MgSO4, filtered and taken to dryness, leaving 2.20 g of pink solid. The pink solid was dissolved in 60 mL of pentane and cooled to −30° C. A white crystalline solid was collected and dried (2.11 g, 79%). The 1H NMR spectrum is complex and is consistent with a mixture of E/Z isomers.

Workup

  1. customresulting in a light pink solution, which
  2. temperaturewas refluxed overnight
  3. customToluene was removed under vacuum
  4. extractionThe solid that deposited was extracted into 150 mL of diethylether
  5. dry with materialThe ether layer was dried with MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-81c9e81a07cb4ba68b949c66dc5db104
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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