O-Phenylenediamine → 1-(4-Cyano-phenyl)-3-[-(1-phenyl-ethylamino)-phenyl]-urea

HRID 49016

Reaction equation

HRID 49016 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].C(=O)([O-])[O-].[K+].[K+].Br[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17].[C:24]([C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=1)#[N:25]>CN(C)C=O>[C:24]([C:26]1[CH:27]=[CH:28][C:29]([NH:32][C:33]([NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])=[O:34])=[CH:30][CH:31]=1)#[N:25]

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 11454(1-Bromoethyl)benzeneHCID 1703804-Cyanophenyl isocyanate

Product 1

HCID 120439691-(4-Cyano-phenyl)-3-[-(1-phenyl-ethylamino)-phenyl]-urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.16 g (10.8 mmol) 1,2-phenylene diamine was dissolved in 10 ml dimethyl formamide, 2.1 g (15 mmol) potassium carbonate and 1.47 ml (10.8 mmol) 1-bromo-1-phenylethane were added with stirring. After 8 hours (h) at rt, most of the starting materials were consumed. Potassium bromide was filtered off, the solvent removed, the mixture redissolved in 20 ml THF and then 1,15 g (8 mmol) 4-cyanophenylisocyanate were slowly added and stirred for another 50 h at rt. The mixture was worked up by filtration, evaporated to dryness, dissolved in ethyl acetate and washed with diluted HCl, sodium carbonate solution and brine.

Workup

  1. custommost of the starting materials were consumed
  2. filtrationPotassium bromide was filtered off
  3. customthe solvent removed
  4. dissolutionthe mixture redissolved in 20 ml THF
  5. stirringstirred for another 50 h at rt
  6. filtrationThe mixture was worked up by filtration
  7. customevaporated to dryness
  8. dissolutiondissolved in ethyl acetate
  9. washwashed with diluted HCl, sodium carbonate solution and brine

Sources & evidence

ORD record
ord-76d8bb49b18e460c92fe6379f655d37e
Source dataset
uspto-grants-2004_03
Patent number
US06706715B2

Linked notes

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