Hexachloroethane → 1-Ethyl-4-nitro-1H-pyrazole

HRID 1487671노트

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HRID 1487671 반응식
Cl[C:2]1[N:6]([CH2:7][CH3:8])[N:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].ClC(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.[Cl-].[Na+].O>[CH2:7]([N:6]1[CH:2]=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=[N:5]1)[CH3:8]

참가 물질

6

반응물 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 584650475-Chloro-1-ethyl-4-nitro-1H-pyrazole

생성물 1

HCID 125652131-Ethyl-4-nitro-1H-pyrazole수율 88.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 57417360Sodium chloride; water용매

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온도
-78 °C

실험 절차

To a solution of 5-chloro-1-ethyl-4-nitro-1H pyrazole (1 equiv) in THF (0.6 M) was added dropwise a 1.0 M solution of lithium bis(trimethylsilyl)amide (2.6 equiv) at −78° C. The reaction mixture was stirred at −78° C. for 30 min before the addition of hexachloroethane (1.5 equiv) in THF (1.2 M). The mixture was stirred at −78° C. for 2.5 h then warmed to room temperature. The reaction was diluted with brine (1.8 M) and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (10-15% ethyl acetate in petroleum ether) to afford the desired product as a white solid (88.2% yield). MS (ESI) m/z 176.0 [M+H]+.

후처리

  1. temperaturethen warmed to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography (10-15% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-e7948c0b803a4f35829f570a8f958ee2
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428509B2

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