Aluminum(III) Chloride → HCID 136048655, compound

HRID 52245Notes

Reaction equation

HRID 52245 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[C:16]([Cl:22])[CH:15]=2)[N:11]([CH3:23])[N:10]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([Cl:22])[CH:15]=2)[N:11]([CH3:23])[N:10]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 214636823-(2-chloro-6-fluorophenyl)-5-(3-chloro-4-methoxyphenyl)-1-methyl-1H-1,2,4-triazole

Product 1

HCID 136048655HCID 136048655, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To benzene (300 ml) are added the crude product of 3-(2-chloro-6-fluorophenyl)-5-(3-chloro-4-methoxyphenyl)-1-methyl 1H-1,2,4-triazole (70.5 g) and anhydrous aluminum chloride (80.0 g), which are heated under reflux for 3 hours with stirring. After cooling to room temperature, the reaction mixture is poured into ice water and extracted with toluene. The organic layer is washed with water, extracted with aqueous solution of 20% NaOH, and the aqueous layer is acidified by adding a concentrated sulfuric acid little by little while cooling with ice and extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 64.2 g of desired compound.

Workup

  1. temperatureare heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with toluene
  4. washThe organic layer is washed with water
  5. extractionextracted with aqueous solution of 20% NaOH
  6. additionby adding a concentrated sulfuric acid little by little
  7. temperaturewhile cooling with ice
  8. extractionextracted with ethyl acetate
  9. washThe organic layer is washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7c3eb304c44496ba5ff4c3a302ccbf0
Source dataset
uspto-grants-1997_04
Patent number
US05616594

Reaction notes

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