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

HRID 1487671ノート

反応式

HRID 1487671 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 125652131-Ethyl-4-nitro-1H-pyrazole収率 88.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360Sodium chloride; water溶媒

反応条件

温度
-78 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-e7948c0b803a4f35829f570a8f958ee2
出典データセット
uspto-grants-2016_08
特許番号
US09428509B2

反応ノート

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