p-Xylyl bromide → 1-(4-methylbenzyl)-3-nitro-1H-pyrazole

HRID 546029

反応式

HRID 546029 の反応式
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1>CN(C)C=O>[CH3:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:6]2[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]2)=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 7721p-Xylyl bromideHCID 24758Sodium hydrideHCID 178526745HCID 178526745、化合物

生成物 1

HCID 70101741-(4-methylbenzyl)-3-nitro-1H-pyrazole収率 82.2%

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 20 min, 4-methylbenzylbromide (426 mg, 2.30 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-(4-methyl-benzyl)-3-nitro-1H-pyrazole (316 mg, 82%) as a white solid: H1-NMR (400 MHz, CDCl3) δ: 2.36 (3H, s), 5.32 (2H, s), 6.87 (1H, d, J=2.3 Hz), 7.19 (4H, s), 7.34 (1H, d, J=2.3 Hz).

後処理

  1. stirringthe mixture was stirred for additional 20 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-0a74d6e706e94597b81e0c482d3ffd78
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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