反应 #171833

反应方程式

9-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide

dimethylformamide dimethylacetal

AcOH

2,4-difluorophenylhydrazine hydrochloride

→

399

收率 31.0%

9-Bromo-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

收率 31.0%

溶剂

toluene

water

反应条件

后处理

1. 1
   浓缩was concentrated
2. 2
   温度the resulting solution heated at 100° C. for 3 h
3. 3
   浓缩The reaction mixture was concentrated
4. 4
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2 (50 ml)
5. 5
   洗涤washed with satd
6. 6
   其他The organic layer was separated (hydrophobic frit)
7. 7
   浓缩concentrated
8. 8
   其他purified by ISCO

实验过程

A stirred suspension of 9-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide (0.70 g; 2.2 mmol) and dimethylformamide dimethylacetal (DMF·DMA, 6 ml) in toluene (5 ml) was heated at 100° C. overnight (16 h) upon which time the reaction mixture was concentrated. To the resulting residue was added AcOH (5 ml), water (0.5 ml) and 2,4-difluorophenylhydrazine hydrochloride (0.56 g; 3.1 mmol) and the resulting solution heated at 100° C. for 3 h. The reaction mixture was concentrated, the residue was dissolved in CH2Cl2 (50 ml) and washed with satd. NaHCO3 (50 ml). The organic layer was separated (hydrophobic frit), concentrated and purified by ISCO to give 399 as a cream-coloured solid (0.31 g; 31%). δH (400 MHz, CDCl3) 3.41 (t, J=5.2, 2H), 4.36 (t, J=5.2, 2H), 6.89 (d, J=8.8, 1H), 7.14-7.20 (m, 2H), 7.27-7.30 (m, 1H), 7.55-7.61 (m, 1H), 7.69 (d, J=2.8, 1H), 8.16 (s, 1H). [M+H]+: 462

来源