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

HRID 2064937노트

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HRID 2064937 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 694302-Oxopropiononitrile용매2회

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5f9d0c71e6b440c5b0a05143ae5aa72f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288419B2

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