1-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone → 58905-18-3

HRID 1649782Notes

Reaction equation

HRID 1649782 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

4

Reactant 2

HCID 7393741-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanoneHCID 4311764Sodium borohydride

Product 1

HCID 66285758905-18-3Yield 46.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

25.6 g (0.1 mole) of 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-1-ethanone are dissolved in 610 ml of methanol, and 6.3 g (0.15 mole) of sodium borohydride are added in portions at 5° to 10° C., while stirring. The mixture is then stirred at room temperature for one hour and heated at the boil for one hour. After the solvent has been distilled off, 250 ml of water and 50 ml of concentrated hydrochloric acid are added to the residue and the mixture is boiled up for 15 minutes. After the reaction mixture has been rendered alkaline with sodium hydroxide solution, the solid reaction product can be filtered off. It is recrystallized from aqueous acetonitrile. 12 g (42% of theory) of 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-1-ethanol of melting point 87° C. are obtained.

Workup

  1. stirringThe mixture is then stirred at room temperature for one hour
  2. temperatureheated at the boil for one hour
  3. distillationAfter the solvent has been distilled off
  4. addition250 ml of water and 50 ml of concentrated hydrochloric acid are added to the residue
  5. customthe solid reaction product
  6. filtrationcan be filtered off
  7. customIt is recrystallized from aqueous acetonitrile

Sources & evidence

ORD record
ord-0ade864e34b94116b5242c34be3200e7
Source dataset
uspto-grants-1990_05
Patent number
US04921870

Reaction notes

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