Sodium Chloride → N-4-Chlorocinnamyl-1,2-phenylenediamine

HRID 1090578Notes

Reaction equation

HRID 1090578 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[Cl:9][C:10]1[CH:19]=[CH:18][C:13]([CH:14]=[CH:15][CH2:16]Cl)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>CN(C)C=O.O>[Cl:9][C:10]1[CH:19]=[CH:18][C:13]([CH:14]=[CH:15][CH2:16][NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH2:8])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 53728250p-Chlorocinnamyl chloride

Product 1

HCID 54229126N-4-Chlorocinnamyl-1,2-phenylenediamineYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

19.6 g of 1,2-phenylenediamine was dissolved in 300 ml of dimethylformamide, to the solution were added 11.3 g of the above-prepared 4-chlorocinnamyl chloride crystals and 12.5 g of potassium carbonate at a room temperature with stirring, and the mixture was stirred for 48 hours under the same condition. After adding water and sodium chloride, the reaction mixture was extracted twice with 1000 ml of chloroform, and the extract was dried over magnesium sulfate and evaporated to remove the solvent under a reduced pressure. Resulting residue was applied to a silica gel column and eluted with hexane/ethyl acetate (3:1), to obtain 12.85 g of the title compound as colorless crystals.

Workup

  1. stirringthe mixture was stirred for 48 hours under the same condition
  2. extractionthe reaction mixture was extracted twice with 1000 ml of chloroform
  3. dry with materialthe extract was dried over magnesium sulfate
  4. customevaporated
  5. customto remove the solvent under a reduced pressure
  6. washeluted with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-df6509ebf0c6476c9db0f28f31052d21
Source dataset
uspto-grants-1992_01
Patent number
US05081246

Reaction notes

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