Cyclohexylamine → N-Cyclohexyl-N'-phenyl-4-phenylenediamine

HRID 1073357Notes

Reaction equation

HRID 1073357 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CS(O)(=O)=O.C1(C)C=CC=CC=1>[C:1]1([NH:7][C:4]2[CH:5]=[CH:6][C:1]([NH:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:2][CH:3]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 7965Cyclohexylamine

Product 1

HCID 92093N-Cyclohexyl-N'-phenyl-4-phenylenediamine

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 1140TolueneSolvent

Procedure

Into a three neck 500 ml flask equipped with a thermometer, stirrer, Dean Stark trap and condenser was charged 18.4 grams of N-phenylquinoneimine, 150 ml toluene, 19.9 cyclohexylamine and 5 drops methanesulfonic acid. The reaction was conducted at 110°C. for 1.5 hours after which time the product was washed with 200 ml water containing 10 grams of Na2S2O4. The product was decanted, filtered and stripped at a pot temperature of 100°C. at 4 mm Hg. 27 grams of N-phenyl-N'-cyclohexyl-p-phenylenediamine were recovered.

Workup

  1. customInto a three neck 500 ml flask equipped with a thermometer, stirrer, Dean Stark trap and condenser
  2. washafter which time the product was washed with 200 ml water containing 10 grams of Na2S2O4
  3. customThe product was decanted
  4. filtrationfiltered
  5. customstripped at a pot temperature of 100°C. at 4 mm Hg
  6. custom27 grams of N-phenyl-N'-cyclohexyl-p-phenylenediamine were recovered

Sources & evidence

ORD record
ord-2803475c97e7430e843b4f248fc76fbb
Source dataset
uspto-grants-1990_11
Patent number
US04968843

Reaction notes

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