Potassium Iodide → HCID 135838255, compound

HRID 1707828Notes

Reaction equation

HRID 1707828 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=3[OH:21])[N:11]=[C:10]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][C:23]=3[OH:29])[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:38]1([SH:44])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>O.CN(C)C=O>[OH:21][C:15]1[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]=1[C:12]1[N:11]=[C:10]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][C:23]=2[OH:29])[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([S:44][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:3][CH:4]=2)[N:13]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 1358281874,4′-[6-(4-Chlorophenyl)-1,3,5-triazine-2,4-diyl]bis[1,3-benzenediol]

Product 1

HCID 135838255HCID 135838255, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a 500 mL round bottomed flask equipped with a magnetic stirrer, condenser, Dean-Stark trap and nitrogen atmosphere are charged 16.1 g (0.0394 mol) of 6-(p-chlorophenyl)-2,4-bis-(2,4-dihydroxyphenyl)-s-triazine, 2.72 g (0.0197 mol) of potassium carbonate, 600 mg of potassium iodide and 150 mL of N,N-dimethylformamide. A pre-heated oil bath (150° C.) is then applied to the stirred brown solution. Thiophenol (4.04 mL, 0.00394 mol) is added all at once through a syringe. The mixture is stirred at 150° C. for 4.5 hours and then allowed to cool to room temperature. The solution is diluted with water and extracted thrice with ethyl acetate. The combined organic layers are washed twice with 0.1N hydrochloric acid and then dried over anhydrous magnesium sulfate. The solvent is then removed under reduced pressure to give a yellow product. There is some unsolubilized material found at the interface in the ethyl acetate extractions of the reaction mixture which is washed with water and triturated with heptane. Both crops of yellow solid are the title compound and are combined to afford the title compound in a yield of 17.5 g (92%); mp>250°.

Workup

  1. customTo a 500 mL round bottomed flask equipped with a magnetic stirrer, condenser
  2. customA pre-heated oil bath (150° C.) is then applied to the stirred brown solution
  3. temperatureto cool to room temperature
  4. extractionextracted thrice with ethyl acetate
  5. washThe combined organic layers are washed twice with 0.1N hydrochloric acid
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent is then removed under reduced pressure
  8. customto give a yellow product
  9. extractionfound at the interface in the ethyl acetate extractions of the reaction mixture which
  10. washis washed with water
  11. customtriturated with heptane

Sources & evidence

ORD record
ord-9c01263b89e443b691e389667e0fb5e4
Source dataset
uspto-grants-1994_10
Patent number
US05354794

Reaction notes

Loading…