1,3,5-Trichlorobenzene → HCID 13531050, compound

HRID 580687Notes

Reaction equation

HRID 580687 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Cl:9][C:10]1[CH:15]=[C:14](Cl)[CH:13]=[C:12]([Cl:17])[CH:11]=1.[C:18](=[O:21])([O-])[O-].[K+].[K+]>CN(C)P(=O)(N(C)C)N(C)C>[ClH:9].[NH2:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:14]1[CH:13]=[C:12]([Cl:17])[CH:11]=[C:10]([O:21][C:18]2[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 79501,3,5-TrichlorobenzeneHCID 11430Potassium CarbonateHCID 115683-Aminophenol

Product 1

HCID 13531050HCID 13531050, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

32.7 g (0.3 mol) of 3-aminophenol, 18.2 g (0.1 mol) of 1,3,5-trichlorobenzene, 28 g (0.2 mol) of anhydrous potassium carbonate and 150 ml of hexamethylphosphoric triamide were charged in a flask equipped with a stirrer. The mixture was maintained at 180° to 190° C. for 24 hours under stirring while passing gaseous nitrogen through it to accomplish the condensation. Then the reaction mixture was treated according to the same procedure as described in Example 1 to obtain 34.4 g of 1,3-bis(3-aminophenoxy)-5-chlorobenzene hydrochloride (yield: 85.8%).

Workup

  1. customequipped with a stirrer
  2. temperatureThe mixture was maintained at 180° to 190° C. for 24 hours
  3. customthe condensation
  4. additionThen the reaction mixture was treated

Sources & evidence

ORD record
ord-774cc0508a0342459631074e18e82b66
Source dataset
uspto-grants-1988_06
Patent number
US04754068

Reaction notes

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