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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
ノート
印刷プレビュー

反応式

HRID 2207960 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol
溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-08eaf025624f4143900d72f23d0a2f81
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09376420B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート