O-Phenylenediamine → 4-[3-(2-{1-[4-Carboxyphenyl]-ethylamino}-phenyl)-ureido]-benzonitrile

HRID 49017

Reaction equation

HRID 49017 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1)#[N:2].[C:12]1([NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18].Br[CH:21]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1)[CH3:22].C(=O)([O-])[O-].[K+].[K+]>C(OCC)C.CN(C=O)C>[C:27]([C:26]1[CH:30]=[CH:31][C:23]([CH:21]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:19][C:10](=[O:11])[NH:9][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[CH3:22])=[CH:24][CH:25]=1)([OH:29])=[O:28]

Participants

7

Reactant 4

HCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 1703804-Cyanophenyl isocyanateHCID 51462254-(1-Bromoethyl)benzoic acid

Product 1

HCID 206351434-[3-(2-{1-[4-Carboxyphenyl]-ethylamino}-phenyl)-ureido]-benzonitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

12.8 g (88.8 mmol) 4-cyanophenylisocyanat were dissolved in 500 ml diethyl ether at rt. 9.6 g (88.8 mmol) o-phenylene diamine were added with stirring. After stirring overnight, the reaction mixture was filtrated and the solid washed with diethylether. The so prepared mono-urea derivative was sufficient pure for further reactions. 3.78 (15 mmol) were dissolved in 30 ml anhydrous dry DMF, 3.44 g (15 mmol) 4-(1-bromoethyl)-benzoic acid and 2 g potassium carbonate were added and stirred for 3 days at rt. The solvent was removed under reduced pressure, the product dissolved in ethyl acetate and extracted with 1 m HCl, water and brine. The organic phase was dried over sodium sulfate and the solvent removed under reduced pressure.

Workup

  1. stirringAfter stirring overnight
  2. filtrationthe reaction mixture was filtrated
  3. washthe solid washed with diethylether
  4. customThe so prepared mono-urea derivative
  5. stirringstirred for 3 days at rt
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe product dissolved in ethyl acetate
  8. extractionextracted with 1 m HCl, water and brine
  9. dry with materialThe organic phase was dried over sodium sulfate
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-5171a0f3ec00423cbedc952e18e7cb9a
Source dataset
uspto-grants-2004_03
Patent number
US06706715B2

Linked notes

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