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Thionyl Chloride → 4-(chloromethyl)-1-phenyl-1H-pyrazole

HRID 914452
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반응식

HRID 914452 반응식
[C:1]1([N:7]2[CH:11]=[C:10]([CH2:12]O)[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:16][CH2:12][C:10]1[CH:9]=[N:8][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:11]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 822983(1-phenyl-1H-pyrazol-4-yl)methanol

생성물 1

HCID 21211624-(chloromethyl)-1-phenyl-1H-pyrazole수율 106.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

(1-Phenyl-1H-pyrazol-4-yl)methanol (6.3 g) synthesized in Reference Example 17 was dissolved in dichloromethane (100 mL) and, after ice-cooling, thionyl chloride (5.59 g) was added thereto, and the mixture was stirred at 0° C. for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1) to give the title compound (7.4 g) as a white solid.

후처리

  1. temperatureafter ice-cooling
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-14b05bdfa4cf48ae9e5231de0184d5cc
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08026370B2

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