O-Phenylenediamine → 1,2-Benzenediamine,N1-(3-phenyl-2-propen-1-yl)-

HRID 1587203

Reaction equation

HRID 1587203 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+].[CH2:15](Cl)[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH2:15]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH2:8])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

HCID 27716631,2-Benzenediamine,N1-(3-phenyl-2-propen-1-yl)-Yield 89.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.24 g of ortho-phenylenediamine was dissolved in 30 ml of dimithylformaide, to the solution were added 2.07 g of potassium carbonate and 1.52 g of cinnamyl chloride, and the mixture was stirred overnight at a room temperature. After adding 100 ml of water, the reaction mixture was extracted twice with 100 ml and 50 ml of chloroform, and the extract was washed with a saturated sodium chloride aqueous solution, dried over magnesium sulfate and evaporated to remove the solvent under a reduced pressure. The resulting residue was applied to a silica gel column and eluted with chloroform, to obtain 2.0 g of the title compound as light brown crystals.

Workup

  1. extractionthe reaction mixture was extracted twice with 100 ml and 50 ml of chloroform
  2. washthe extract was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto remove the solvent under a reduced pressure
  6. washeluted with chloroform

Sources & evidence

ORD record
ord-b0b86372d756477d9cfc48622dbf0d6f
Source dataset
uspto-grants-1993_06
Patent number
US05216150

Linked notes

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