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Sodium Sulfite → (2E)-3-(5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)-N-(4-((methylsulfinyl)methyl)phenyl)acrylamide

HRID 30726
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인쇄 미리보기

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HRID 30726 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][S:26][CH3:27])=[CH:21][CH:20]=2)=[O:17])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:36])C=1.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][S:26]([CH3:27])=[O:36])=[CH:23][CH:24]=2)=[O:17])=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 69210621(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-{4-[(methylthio)methyl]phenyl}acrylamide

생성물 1

HCID 69210481(2E)-3-(5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)-N-(4-((methylsulfinyl)methyl)phenyl)acrylamide수율 54.4%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
0 °C

실험 절차

A mixture of (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-{4-[(methylthio)methyl]phenyl}acrylamide (600 mg), m-chloroperbenzoic acid (387 mg) and tetrahydrofuran (50 mL) was stirred at 0° C. for 20 min. A saturated aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate, and then with saturated brine, dried (MgSO4) and concentrated. The obtained solid was recrystallized from acetone-hexane to give (2E)-3-(5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)-N-(4-((methylsulfinyl)methyl)phenyl)acrylamide (340 mg, yield 54%) as colorless prism crystals. melting point: 240-241° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate
  3. dry with materialwith saturated brine, dried (MgSO4)
  4. concentrationconcentrated
  5. customThe obtained solid was recrystallized from acetone-hexane

출처 및 근거

ORD 기록
ord-1e6f78d5002d4489be4d29faf1bda012
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07423159B2

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