Hexachloroethane → 5-chloro-1-isopropyl-4-nitro-1H-pyrazole

HRID 1487667노트

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HRID 1487667 반응식
[CH:1]([N:4]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[N:5]1)([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:22]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.[Cl-].[Na+].O>[Cl:22][C:8]1[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][C:7]=1[N+:9]([O-:11])=[O:10]

참가 물질

6

반응물 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 134698241-Isopropyl-4-nitro-1H-pyrazole

생성물 1

HCID 584648025-chloro-1-isopropyl-4-nitro-1H-pyrazole수율 84%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 57417360Sodium chloride; water용매

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온도
-78 °C

실험 절차

To a solution of 1-isopropyl-4-nitro-1H-pyrazole (1 equiv) in THF (0.65 M) was added dropwise a 1.0 M solution of lithium bis(trimethylsilyl)amide (2.6 equiv) in THF at −78° C. The reaction was stirred at −78° C. for 30 min before the addition of hexachloroethane (1.5 equiv) in THF (1.63 M). The reaction was stirred at −78° C. for 2.5 h then warmed to room temperature. The reaction was diluted with brine 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 (10-20% ethyl acetate in petroleum ether) to afford the desired product (84% yield) as a white solid. MS (ESI) m/z 190.1 [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 (10-20% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-81cea2fa3b394d6da1397146639382e1
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428509B2

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