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Hydrochloric Acid → 1-(2-chloro-phenyl)-5-(3'-methylsulfanyl-biphenyl-4-yl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole

HRID 2207960
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HRID 2207960 반응식
[F:1][C:2]([F:25])([C:21]([F:24])([F:23])[F:22])[C:3](=O)[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH3:19])[CH:13]=2)=[CH:8][CH:7]=1.Cl.[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][NH2:35].Cl>C(O)C>[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[CH:5]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH3:19])[CH:13]=3)=[CH:8][CH:7]=2)[CH2:4][C:3]([C:2]([F:25])([F:1])[C:21]([F:24])([F:23])[F:22])=[N:35]1
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 4432872-Chlorophenylhydrazine hydrochlorideHCID 1317359334,4,5,5,5-Pentafluoro-1-(3'-methylsulfanyl-biphenyl-4-yl)-pent-1-en-3-one

생성물 1

HCID 1184319481-(2-chloro-phenyl)-5-(3'-methylsulfanyl-biphenyl-4-yl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole수율 57.4%

시약·촉매·용매 1

HCID 702Ethanol
용매

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온도
100 °C

실험 절차

4,4,5,5,5-Pentafluoro-1-(3′-methylsulfanyl-biphenyl-4-yl)-pent-1-en-3-one (200.0 mg, 0.54 mmol) prepared in Step 2 of Preparation 2, 2-chlorophenylhydrazine hydrochloride (115.0 mg, 0.64 mmol) and conc. hydrochloric acid (200.0 uL) were added to ethanol (5.0 mL). The reaction mixture was stirred at 100° C. for 18 hours, quenched with a saturated solution of sodium hydrogen carbonate, and then extracted with ethyl acetate three times. The combined extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/60) to give 154.0 mg of the titled compound as a yellow liquid.

후처리

  1. customquenched with a saturated solution of sodium hydrogen carbonate
  2. extractionextracted with ethyl acetate three times
  3. extractionThe combined extract
  4. washwas washed with brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow liquid residue
  8. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/60)

출처 및 근거

ORD 기록
ord-08eaf025624f4143900d72f23d0a2f81
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09376420B2

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