Thionyl Chloride → 1-benzyl-4-chloromethyl-5-phenyl-1H-pyrazole

HRID 349927노트

반응식

HRID 349927 반응식
S(Cl)([Cl:3])=O.[CH2:5]([N:12]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:15]([CH2:23]O)[CH:14]=[N:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[CH2:5]([N:12]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:15]([CH2:23][Cl:3])[CH:14]=[N:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 23025093(1-benzyl-5-phenyl-1H-pyrazol-4-yl)methanol

생성물 1

HCID 230250441-benzyl-4-chloromethyl-5-phenyl-1H-pyrazole수율 96.4%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Thionyl chloride (4.35 g) was added to a solution of (1-benzyl-5-phenyl-1H-pyrazol-4-yl)methanol (8.06 g) in toluene (100 ml) dropwise at 0° C., and the mixture was stirred at room temperature for one hour and then refluxed for ten minutes. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate and then with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and 1-benzyl-4-chloromethyl-5-phenyl-1H-pyrazole (8.31 g, yield: 96%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

후처리

  1. temperaturerefluxed for ten minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5da7c8d0132c42a28530ec8bb0aaa86b
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179823B1

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