Triethylamine → 2,4-difluoro-alpha-(1H-1,2,4-triazol-1-yl)acetophenone hydrochloride

HRID 728337

反応式

HRID 728337 の反応式
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C(N(CC)CC)C.[Cl:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24])=[O:16]>C(OCC)(=O)C>[ClH:13].[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[C:15](=[O:16])[CH2:14][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 92571H-1,2,4-TriazoleHCID 5880832-Chloro-1-(2,4-difluorophenyl)ethanone

生成物 1

HCID 130596992,4-difluoro-alpha-(1H-1,2,4-triazol-1-yl)acetophenone hydrochloride収率 41.6%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a mixture of 1,2,4-triazole (30.4 g, 0.44 mole) and triethylamine (15.1 g, 0.15 mole) in refluxing ethyl acetate (186 ml) was added a solution of 2-chloro-2',4'-difluoroacetophenone (38.1 g, 0.2 mole) in ethyl acetate (80 ml). The mixture was refluxed for six hours then cooled to room temperature and the insolubles were removed by filtration. the filtrate was washed with water (2×200 ml) and then the solvent was removed by distillation at reduced pressure. The crude product was dissolved in ethyl acetate (150 ml) then 25% w/v HCl gas in isopropanol was added. The mixture was granulated at 0° C. for one hour and then the solid was collected by filtration and dried to give the title compound (21.6 g, 40%), melting point 167°-170° C. IR (KBr) and NMR (DMSO) were consistent with the desired structure.

後処理

  1. temperatureThe mixture was refluxed for six hours
  2. customthe insolubles were removed by filtration
  3. washthe filtrate was washed with water (2×200 ml)
  4. customthe solvent was removed by distillation at reduced pressure
  5. dissolutionThe crude product was dissolved in ethyl acetate (150 ml)
  6. additionwas added
  7. filtrationthe solid was collected by filtration
  8. customdried

出典と根拠

ORDレコード
ord-06356f02d6c24fce8073f6e767320c8f
出典データセット
uspto-grants-1991_09
特許番号
US05047548

関連ノート

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