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

HRID 1487667ノート

反応式

HRID 1487667 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 584648025-chloro-1-isopropyl-4-nitro-1H-pyrazole収率 84%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 57417360Sodium chloride; water溶媒

反応条件

温度
-78 °C

実験手順

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]+.

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 (10-20% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-81cea2fa3b394d6da1397146639382e1
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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