Potassium Carbonate → N,N'-bis-(2,6-diisopropylphenyl)-N"-(4-chloromethylphenyl) methylguanidine

HRID 1707913Notes

Reaction equation

HRID 1707913 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14]([NH:16][C:17]1[C:22]([CH:23]([CH3:25])[CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=1[CH:26]([CH3:28])[CH3:27])=[NH:15])([CH3:3])[CH3:2].[Cl:29][CH:30](Cl)[C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(C)=CC=CC=1>[CH:23]([C:22]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:26]([CH3:28])[CH3:27])[C:17]=1[NH:16][C:14]([NH:13][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:10]([CH3:12])[CH3:11])=[N:15][CH2:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][Cl:29])=[CH:32][CH:33]=1)([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5200171-(Dichloromethyl)-4-methylbenzeneHCID 178418589HCID 178418589, compound

Product 1

HCID 15217299N,N'-bis-(2,6-diisopropylphenyl)-N"-(4-chloromethylphenyl) methylguanidineYield 40.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

11.4 g (0.03 mole) of N,N'-bis-(2,6-diisopropylphenyl) guanidine, 5.7 g (0.033 mole) of α,α-dichloro-p-xylene and 2.1 g (0.015 mole) of anhydrous potassium carbonate were added to 50 ml of xylene. 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 6.3 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-6c67790f96b04bcdb891fa7a93f2c95d
Source dataset
uspto-grants-1994_10
Patent number
US05356749

Reaction notes

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