N-Phenyl-p-phenylenediamine → N,N'-Dicyclohexylurea

HRID 393509Notes

Reaction equation

HRID 393509 reaction equation
C1C=CC(NC2C=CC(N)=CC=2)=CC=1.[OH:15]C1C2N=NNC=2C=CC=1.[CH:25]1([N:31]=[C:32]=[N:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C1COCC1>[C:32]([NH:31][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)([NH:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)=[O:15]

Participants

5

Reactant 3

HCID 7564N-Phenyl-p-phenylenediamineHCID 10868DicyclohexylcarbodiimideHCID 178418300HCID 178418300, compound

Product 1

HCID 4277N,N'-DicyclohexylureaYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.65 g (8.98 mmol) of 4-aminodiphenylamine, 1.77 g (8.98 mmol) of intermediate 3.2 and 1.27 g (9.42 mmol) of hydroxybenzotriazole are dissolved in 40 ml of THF in a 100 ml flask, under a nitrogen atmosphere. When all have dissolved, 1.94 g (9.42 mmol) of 1,3-dicyclohexylcarbodiimide is added and the reaction medium is left under agitation for 15 hours. The precipitate of dicyclohexylurea formed is filtered and rinsed with ethyl acetate. The filtrate is evaporated under vacuum and the evaporation residue is taken up in ethyl acetate, it then forms a precipitate which is filtered and rinsed using the same solvent. A greenish solid is obtained with a yield of 65%. The product obtained is sufficiently pure to be used directly in the following stage. Melting point: 192-195° C.

Workup

  1. dissolutionWhen all have dissolved

Sources & evidence

ORD record
ord-fdf4574536dd453f8d33023c484f6d8b
Source dataset
uspto-grants-2004_10
Patent number
US06809090B2

Reaction notes

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