Potassium Carbonate → N,N'-bis-(2,6-diethylphenyl)-N"-(3-chloromethylphenyl) methylguanidine

HRID 5759

Reaction equation

HRID 5759 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([NH:14][C:15]1[C:20]([CH2:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:23][CH3:24])=[NH:13])[CH3:2].[Cl:25][CH:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([NH:14][C:15]1[C:20]([CH2:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:23][CH3:24])=[N:13][CH2:33][C:29]1[CH:30]=[CH:31][CH:32]=[C:27]([CH2:26][Cl:25])[CH:28]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5874201-(Dichloromethyl)-3-methylbenzeneHCID 178418671HCID 178418671, compound

Product 1

HCID 86747217N,N'-bis-(2,6-diethylphenyl)-N"-(3-chloromethylphenyl) methylguanidineYield 32.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9.7 g (0.03 mole) of N,N'-bis-(2,6-diethylphenyl) guanidine, 5.7 g (0.033 mole) of α,α-dichloro-m-xylene and 2.1 g (0.015 mole) of anhydrous potassium carbonate were added to 50 ml of toluene. The thus-formed mixture was then refluxed under heating for 10 hours. After the mixture had been allowed to cool, the insoluble substance was removed by filtration. The thus-obtained filtrate was washed with water and then concentrated for the purpose of recovering the solvent and unreacted raw materials to obtain a slightly yellow crystal. The crystal was then recrystallized from benzene to obtain 4.5 g of white powder.

Workup

  1. temperatureThe thus-formed mixture was then refluxed
  2. temperatureunder heating for 10 hours
  3. temperatureto cool
  4. customthe insoluble substance was removed by filtration
  5. washThe thus-obtained filtrate was washed with water
  6. concentrationconcentrated for the purpose
  7. customof recovering the solvent and unreacted raw materials
  8. customto obtain a slightly yellow crystal
  9. customThe crystal was then recrystallized from benzene

Sources & evidence

ORD record
ord-6fb2d39ee99944cc9f9143eb8ab5677c
Source dataset
uspto-grants-1993_09
Patent number
US05246810

Linked notes

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