Ethyl chloroformate → 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-ethoxycarbonyl-N-(3-ethylthiopropyl)amino]-4-trifluoromethylsulfonylpyrazole

HRID 2109917노트

반응식

HRID 2109917 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([Cl:14])[C:5]=1[N:15]1[C:19]([NH:20][CH2:21][CH2:22][CH2:23][S:24][CH2:25][CH3:26])=[C:18]([S:27]([C:30]([F:33])([F:32])[F:31])(=[O:29])=[O:28])[C:17]([C:34]#[N:35])=[N:16]1.Cl[C:37]([O:39][CH2:40][CH3:41])=[O:38].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[Cl:14][C:6]1[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=[C:4]([Cl:3])[C:5]=1[N:15]1[C:19]([N:20]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:21][CH2:22][CH2:23][S:24][CH2:25][CH3:26])=[C:18]([S:27]([C:30]([F:33])([F:32])[F:31])(=[O:28])=[O:29])[C:17]([C:34]#[N:35])=[N:16]1

참가 물질

7

반응물 4

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 866002281-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyano-5-(3-ethylthiopropylamino)-4-trifluoromethylsulfonylpyrazole

생성물 1

HCID 866002311-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-ethoxycarbonyl-N-(3-ethylthiopropyl)amino]-4-trifluoromethylsulfonylpyrazole수율 81%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
20 °C

실험 절차

Sodium hydride (0.032 g, 60%, 0.8 mmol) was added to a solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(3-ethylthiopropylamino)-4-trifluoromethylsulfonylpyrazole (0.3 g, 0.54 mmol) in tetrahydrofuran 20° C. under nitrogen. The mixture was stirred at 20° C. for one hour then ethyl chloroformate (0.121 g, 1.1 mmol) was added. The mixture was stirred at 20° C. for 5 hours, then poured into saturated ammonium chloride and ethyl acetate. The organic layer was washed with water and brine, dried (sodium sulfate), evaporated to provide and purified by chromatography on silica gel eluting with heptane-ethyl acetate (4:1) to give 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-ethoxycarbonyl-N-(3-ethylthiopropyl)amino]-4-trifluoromethylsulfonylpyrazole as an oil (Compound number 3-14, 0.278 g, 81% yield), 19F: −63.9; −77.9.

후처리

  1. stirringThe mixture was stirred at 20° C. for 5 hours
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. customevaporated
  5. customto provide
  6. custompurified by chromatography on silica gel eluting with heptane-ethyl acetate (4:1)

출처 및 근거

ORD 기록
ord-a67d097e7a6d4a7fb5c4e4a815b0eeeb
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517877B2

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