Dimethylformamide → methyl 1-(4-nitrobenzyl)-1H-1,2,4-triazole-5-carboxylate

HRID 30685

反応式

HRID 30685 の反応式
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1.[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1)([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:2]2[C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:4][CH:5]=[N:1]2)=[CH:15][CH:14]=1)([O-:12])=[O:11]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 178499122HCID 178499122、化合物

生成物 1

HCID 69209378methyl 1-(4-nitrobenzyl)-1H-1,2,4-triazole-5-carboxylate収率 12.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of methyl 1H-1,2,4-triazole-3-carboxylate (7.06 g), 4-nitrobenzyl bromide (10 g), potassium carbonate (16.6 g) and N,N-dimethylformamide (60 ml) was stirred at room temperature for 4 hrs. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give methyl 1-(4-nitrobenzyl)-1H-1,2,4-triazole-5-carboxylate (1.50 g, 12%) as crystals from a fraction eluted with hexane-ethyl acetate (1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 126-130° C.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-45fd186c4b9f4f51b637c81be0fea8c5
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

関連ノート

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