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

HRID 5760Notes

Reaction equation

HRID 5760 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[NH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[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=CC=CC=1>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:15][CH2:37][C:34]2[CH:35]=[CH:36][C:31]([CH2:30][Cl:29])=[CH:32][CH:33]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5200171-(Dichloromethyl)-4-methylbenzeneHCID 178418585HCID 178418585, compound

Product 1

HCID 86747218N,N'-bis-(2-phenylphenyl)-N"-(4-chloromethylphenyl) methylguanidineYield 20.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10.9 g (0.03 mole) of N,N'-bis-(2-phenylphenyl) 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 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 brown powder. The power was then recrystallized from acetone to obtain 3.1 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 brown powder
  9. customThe power was then recrystallized from acetone

Sources & evidence

ORD record
ord-6b289f54e6794a3998880c4a3d4f3dbc
Source dataset
uspto-grants-1993_09
Patent number
US05246810

Reaction notes

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