Water → 5-(4-chlorobenzoyl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole

HRID 443039Notes

Reaction equation

HRID 443039 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:20])[N:8]=2)=[CH:4][CH:3]=1.[OH2:23]>C(O)(=O)C>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([C:7]2[N:11]([CH3:12])[N:10]=[C:9]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:20])[N:8]=2)=[O:23])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 154110235-(4-chlorobenzyl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole

Product 1

HCID 539997465-(4-chlorobenzoyl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2.0 g of 5-(4-chlorobenzyl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole in 20 ml of acetic acid at 10° C., was added 1.2 g of chromic anhydride. After stirring at room temperature overnight, the reaction mixture was poured into iced water and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturatedaqueous sodium hydrogen carbonate solution and then with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to afford 1.7 g of 5-(4-chlorobenzoyl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with a saturatedaqueous sodium hydrogen carbonate solution
  3. dry with materialwith water, dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a3df63239964019a54f650a79db18e6
Source dataset
uspto-grants-1999_04
Patent number
US05892048

Reaction notes

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