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

HRID 610622노트

반응식

HRID 610622 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1828e18fd7864d4eae77a36447b9de93
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998623

반응 노트

불러오는 중…