Benzyl Bromide → 1-benzyl-3-nitro-1H-pyrazole

HRID 546020

反応式

HRID 546020 の反応式
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O>[CH2:11]([N:6]1[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178526745HCID 178526745、化合物

生成物 1

HCID 9736491-benzyl-3-nitro-1H-pyrazole収率 84.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-nitro-1H-pyrazole (prepared in example 3, 200 mg, 1.77 mmol) in anhydrous N,N-dimethylformamide (2 mL), a 60% dispersion of sodium hydride in mineral oil (92 mg, 2.30 mmol) was added while stirring under nitrogen. After the effervescence ceased and the mixture was stirred for additional 10 min, benzylbromide (273 μL, 2.33 mmol) was added. The mixture was continued to stir under nitrogen for an additional 2 h. The solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 2% methanol/methylene chloride to 5% methanol/methylene chloride) afforded 1-benzyl-3-nitro-1H-pyrazole (303 mg, 84%) as a white solid: H1-NMR (400 MHz, CDCl3) δ: 5.33 (2H, s), 6.84 (1H, d, J=2.7 Hz), 7.26 (2H, m), 7.32 (3H, m), 7.40 (1H, d, J=1.5 Hz).

後処理

  1. stirringthe mixture was stirred for additional 10 min
  2. stirringto stir under nitrogen for an additional 2 h
  3. customThe solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 2% methanol/methylene chloride to 5% methanol/methylene chloride)

出典と根拠

ORDレコード
ord-4386fe748a4843d1b23c1514536c0660
出典データセット
uspto-grants-2011_05
特許番号
US07935699B2

関連ノート

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