O-Phenylenediamine → o-Oleoylaminoaniline

HRID 892876Notes

Reaction equation

HRID 892876 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([OH:35])(=O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[C:36]1([NH2:43])[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[NH2:42]>C(Cl)Cl>[C:16]([NH:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[NH2:43])(=[O:35])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 10868DicyclohexylcarbodiimideHCID 445639Oleic Acid

Product 1

HCID 42604663o-OleoylaminoanilineYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N'-Dicyclohexylcarbodiimide (2.27 g) was added to a solution of 2.82 g of oleic acid and 1.62 g of o-phenylenediamine in 50 ml of methylene chloride with stirring under ice cooling. The mixture was stirred at room temperature for one night. After completion of the reaction insoluble matter was filtered, followed by removal of the solvent by evaporation. The residue obtained was purified by silica gel column chromatography to obtain 2.84 g of the objective compound (yield: 76%).

Workup

  1. stirringThe mixture was stirred at room temperature for one night
  2. filtrationAfter completion of the reaction insoluble matter was filtered
  3. customfollowed by removal of the solvent by evaporation
  4. customThe residue obtained
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-113d875ef41f40b19c7720443b250126
Source dataset
uspto-grants-1992_06
Patent number
US05120738

Reaction notes

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