Ethyl Acetate → 1-(4-Methoxybenzyl)-1,2,4-triazole

HRID 610622ノート

反応式

HRID 610622 の反応式
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[OH-].[Na+].[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1.C(OCC)(=O)C>CN(C)C=O.O>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:12][CH:11]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 14798Sodium HydroxideHCID 699934-Methyloxybenzyl chloride

生成物 1

HCID 108453281-(4-Methoxybenzyl)-1,2,4-triazole収率 69%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

1,2,4-Triazole (7.5 g, 0.109 mol) was dissolved in dimethylformamide (50 mL) and stirred under a nitrogen atmosphere in an ice bath at 10° C. while partially ground pellets of sodium hydroxide (17.5 g, 0.438 mol) were added in one portion causing an exotherm to about 25° C. A solution of 4-methoxybenzyl chloride (15 mL, 0.111 mol) in DMF was added dropwise over five minutes at 25° C. After stirring at room temperature for four hours, ethyl acetate and water were added. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed four times with water and once with brine and dried over magnesium sulfate. The mixture was filtered and the filtrate solvent evaporated in vacuo to afford the title product as an oil in 69% yield; 14.15 g; 1H NMR (CDCl3) δ 8.00 (s, 1), 7.93 (s, 1), 7.19 (d, 2), 6.88 (d, 2), 5.23 (s, 2), 3.78 (s, 3). mass spectrum: m/z 109 (M+1).

後処理

  1. additionwere added in one portion
  2. customto about 25° C
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed four times with water
  6. dry with materialonce with brine and dried over magnesium sulfate
  7. filtrationThe mixture was filtered
  8. customthe filtrate solvent evaporated in vacuo

出典と根拠

ORDレコード
ord-1828e18fd7864d4eae77a36447b9de93
出典データセット
uspto-grants-1999_12
特許番号
US05998623

反応ノート

読み込み中…