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Methyl iodide → 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(3-ethylthiopropyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole

HRID 2109915
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HRID 2109915 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([NH:18][CH2:19][CH2:20][CH2:21][S:22][CH2:23][CH3:24])=[C:16]([S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])[C:15]([C:32]#[N:33])=[N:14]1.[H-].[Na+].I[CH3:37].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[C:17]([N:18]([CH2:19][CH2:20][CH2:21][S:22][CH2:23][CH3:24])[CH3:37])=[C:16]([S:25]([C:28]([F:31])([F:30])[F:29])(=[O:26])=[O:27])[C:15]([C:32]#[N:33])=[N:14]1
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참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 866002281-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyano-5-(3-ethylthiopropylamino)-4-trifluoromethylsulfonylpyrazole

생성물 1

HCID 866002291-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(3-ethylthiopropyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole수율 57%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(3-ethylthiopropylamino)-4-trifluoromethylsulfonylpyrazole (2.0 g, 3.6 mmol) in tetrahydrofuran at 20° C. under nitrogen, was added sodium hydride (0.461 g, 60% in oil, 11.5 mmol), and stirred for 0.5 hour. Iodomethane (2.065 g, 14.4 mmol) was added and the mixture stirred for 4.5 hours at 20° C., then allowed to stand for 2.5 days. The mixture was added to ethyl acetate and saturated ammonium chloride solution. The organic layer was washed with water and brine, dried (sodium sulfate), evaporated and chromatographed on silica gel eluting with heptane-ethyl acetate (3:1) to give 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(3-ethylthiopropyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole as a light brown solid (Compound number 2-14, 1.3 g, 57% yield), mp 89° C.

후처리

  1. stirringthe mixture stirred for 4.5 hours at 20° C.
  2. waitto stand for 2.5 days
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. customchromatographed on silica gel eluting with heptane-ethyl acetate (3:1)

출처 및 근거

ORD 기록
ord-b39d6be940c44997b5a3e3e28a9c3890
출처 데이터셋
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07517877B2

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