Ethyl Acetate → 3-(2-chloro-6-fluorophenyl)-5-(3-chloro 4-hydroxymethylphenyl)-1-methyl-1H-1,2,4-triazole

HRID 52244

Reaction equation

HRID 52244 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]([CH3:17])[N:15]=[C:14]([C:18]3[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])[N:13]=2)=[CH:8][C:7]=1[Cl:26])(=O)C.[OH-].[Na+].C(OCC)(=O)C>C(O)C.O>[Cl:25][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([F:24])[C:18]=1[C:14]1[N:13]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][OH:4])=[C:7]([Cl:26])[CH:8]=2)[N:16]([CH3:17])[N:15]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 214636815-(4-acetoxymethyl-3-chlorophenyl)-3-(2-chloro-6-fluorophenyl) 1-methyl-1H-1,2,4-triazole

Product 1

HCID 214636723-(2-chloro-6-fluorophenyl)-5-(3-chloro 4-hydroxymethylphenyl)-1-methyl-1H-1,2,4-triazoleYield 67.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5-(4-acetoxymethyl-3-chlorophenyl)-3(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole (11.1 g) is dissolved in a mixed solvent of ethanol (50 ml) and water (20 ml), added with sodium hydroxide (2.3 g) and heated under reflux for 1 hour with stirring. After cooling to room temperature, the reaction mixture is added with ethyl acetate and washed with water. Then, it is dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain crude solid. The crude solid is washed with mixed solvent of hexane-ethanol to give 6.7 g of desired compound (melting point: 111°-113° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. washwashed with water
  4. dry with materialThen, it is dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain crude solid
  7. washThe crude solid is washed with mixed solvent of hexane-ethanol

Sources & evidence

ORD record
ord-ba6c218d0dfa458986e4da9c49c716cb
Source dataset
uspto-grants-1997_04
Patent number
US05616594

Linked notes

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