Hydrochloric Acid → 2-(5-Chloro-2,4-dihydroxyphenyl)-4,6-bis-(2,4-dimethylphenyl)-s-triazine

HRID 1683453Notes

Reaction equation

HRID 1683453 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=2[CH3:15])[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[CH3:23])[N:3]=1.ClCC(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].[Cl:34][C:35]1[CH:41]=[CH:40][C:38]([OH:39])=[CH:37][C:36]=1[OH:42].Cl>O>[Cl:34][C:35]1[C:36]([OH:42])=[CH:37][C:38]([OH:39])=[C:40]([C:2]2[N:3]=[C:4]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=3[CH3:23])[N:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=3[CH3:15])[N:7]=2)[CH:41]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 17314-ChlororesorcinolHCID 124181,1,1,2-TetrachloroethaneHCID 710591,3,5-Triazine, 2-chloro-4,6-bis(2,4-dimethylphenyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 1358435862-(5-Chloro-2,4-dihydroxyphenyl)-4,6-bis-(2,4-dimethylphenyl)-s-triazineYield 32.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a 1 L three-necked, round-bottomed flask equipped with a magnetic stirrer, thermometer, condenser, and a nitrogen atmosphere are charged 20.0 g (61.9 mmol) of 2-chloro-4,6-bis-(2,4-dimethylphenyl)-s-triazine and 50 mL of tetrachloroethane. The mixture is warmed to dissolve the solids and 8.24 g (62.0 mmol) of aluminum chloride are added in small portions all at once followed by 9.00 g (62.1 retool) of 4-chlororesorcinol. The mixture is stirred at 120° C. for four hours. After cooling to room temperature 50 mL of water and 10 mL of concentrated hydrochloric acid are added and the mixture is refluxed for two hours. After cooling, the mixture is extracted thrice with ethyl acetate and the combined organic layers are dried over anhydrous magnesium sulfate and filtered. The solvent is removed under reduced pressure to yield a yellow solid. Recrystallization from ethyl acetate/heptane affords 8.65 g of the title compound as a yellow solid.

Workup

  1. customTo a 1 L three-necked, round-bottomed flask equipped with a magnetic stirrer
  2. temperatureThe mixture is warmed
  3. additionare added in small portions
  4. additionare added
  5. temperaturethe mixture is refluxed for two hours
  6. temperatureAfter cooling
  7. extractionthe mixture is extracted thrice with ethyl acetate
  8. dry with materialthe combined organic layers are dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customThe solvent is removed under reduced pressure
  11. customto yield a yellow solid
  12. customRecrystallization from ethyl acetate/heptane

Sources & evidence

ORD record
ord-c6c8d04a117445fc8ff8eaac8b791de8
Source dataset
uspto-grants-1997_06
Patent number
US05637706

Reaction notes

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