Nitrogen → 6-(3-Nitro-pyrazol-1-yl)-hexan-2-one

HRID 2064937

反応式

HRID 2064937 の反応式
N#N.[N+:3]([C:6]1[NH:10][N:9]=[CH:8][CH:7]=1)([O-:5])=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[CH3:23]>C(C#N)(C)=O.CC(=O)OCC.O>[N+:3]([C:6]1[CH:7]=[CH:8][N:9]([CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[CH3:23])[N:10]=1)([O-:5])=[O:4]

参加物

8

反応物 4

HCID 947NitrogenHCID 10796Cesium carbonateHCID 250616-Bromohexan-2-oneHCID 1234193-Nitropyrazole

生成物 1

HCID 620232696-(3-Nitro-pyrazol-1-yl)-hexan-2-one

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 694302-Oxopropiononitrile溶媒2 回

反応条件

温度
80 °C

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 5-nitro-1H-pyrazole (3.69 g, 29.35 mmol) and Cs2CO3 (10.53 g, 32.28 mmol) in AcCN (34.0 mL) was treated with a solution of 6-bromo-hexan-2-one (5.78 g, 32.28 mmol) in AcCN (26.0 mL). The reaction mixture was stirred at 80° C. for 2 h. Water (123 mL) and EA (185 mL) were added to the cooled reaction mixture. The aq. layer was extracted with EA (185 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (50:50 hept-EA) gave the title compound. TLC: rf (50:50 hept-EA)=0.21. LC-MS-conditions 02: tR=0.82 min; [M+H]+=212.28.

後処理

  1. extractionThe aq. layer was extracted with EA (185 mL)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (50:50 hept-EA)

出典と根拠

ORDレコード
ord-5f9d0c71e6b440c5b0a05143ae5aa72f
出典データセット
uspto-grants-2012_10
特許番号
US08288419B2

関連ノート

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