Water → HCID 53921289, compound

HRID 443041Notes

Reaction equation

HRID 443041 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[N:12]([CH3:13])[N:11]=[C:10]([C:14]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[N:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:24][Mg]Br.S(=O)(=O)(O)O.O>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH3:13])[N:11]=[C:10]([C:14]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[N:9]=2)([OH:7])[CH3:24])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 539997465-(4-chlorobenzoyl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazoleHCID 178418573HCID 178418573, compound

Product 1

HCID 53921289HCID 53921289, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under an atmosphere of nitrogen, to a solution of 1.5 of 5-(4-chlorobenzoyl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H 1,2,4-triazole in diethl ether at -70° C. was added dropwise 12 ml of methylmagnesium bromide. After 1 hour, the reaction mixture was warmed to room temperature stirred overnight, Then 36 ml of a 2N aqueous solution of sulfuric acid was added to the solution under iced-cooling, the mixture was poured into iced water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gelchromatography to afford 1.3 g of 5-(4-chloro-α-hydroxy-α-methylbenzyl)-3-(2-chloro-6-fluorophenyl)-1-methyl 1H-1,2,4-triazole. mp.198°-200° C.

Workup

  1. temperatureunder iced-cooling
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d5ab59a829844c982e485235275e4f8
Source dataset
uspto-grants-1999_04
Patent number
US05892048

Reaction notes

Loading…