Dimethylformamide → 1-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

HRID 1067926Notes

Reaction equation

HRID 1067926 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])=[O:4].N1C=[CH:16][N:15]=[N:14]1.[OH-].[Na+].[CH3:20][N:21](C)C=O>>[Cl:12][C:6]1[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][N:15]1[CH:16]=[N:21][CH:20]=[N:14]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 202502,2',4'-TrichloroacetophenoneHCID 178418936HCID 178418936, compound

Product 1

HCID 7393741-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanoneYield 25%

Conditions

Temperature
80 °C

Procedure

10 g (44.8 mmol) of 2,2′,4′-trichloroacetophenone were added portionwise at room temperature to a solution of 9.3 g (134 mmol) of triazole in 50 ml of dimethylformamide and stirred at 80° C. for 16 hours. The reaction mixture was added to 100 ml of 2N sodium hydroxide solution and extracted three times with 100 ml of ethyl acetate each time. The combined organic phases were dried over magnesium sulphate and concentrated in a vacuum. The crude product was purified by column chromatography on silica gel (ethyl acetate/methanol 100:5). 2.8 g (25%) of 1-(2,4-dichlorophenyl)-2-[1,2,4]triazol-1-yl-ethanone were obtained as a yellow-brown solid.

Workup

  1. extractionextracted three times with 100 ml of ethyl acetate each time
  2. dry with materialThe combined organic phases were dried over magnesium sulphate
  3. concentrationconcentrated in a vacuum
  4. customThe crude product was purified by column chromatography on silica gel (ethyl acetate/methanol 100:5)

Sources & evidence

ORD record
ord-92ad3ac714dd4354839666188c6f2f85
Source dataset
uspto-grants-2001_06
Patent number
US06248901B1

Reaction notes

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