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

HRID 543201

반응식

HRID 543201 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

To a mixture of 1,2,4-triazole (30.4 g, 0.44M) and triethylamine (15.1 g, 0.15M) in refluxing ethyl acetate (186 ml) was added a solution of 2-chloro-2',4'-difluoroacetophenone (38.1 g, 0.2M) 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%), m.p. 167°-170° C. IR (KBr) and nmr (DMSO) were consistent with the desired structure.

후처리

  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

출처 및 근거

ORD 기록
ord-b5676e84980549b5b37d45d478f024b5
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04661507

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