反応 #213868

反応方程式

6-chloro-1,3-dioxo-1H-benz[de]-isoquinoline-2(3H)-acetic acid

1-decanethiol

sodium carbonate

→

title product

収率 60.8%

1,3-Dioxo-6-(decylthio)-1H-benz[de]isoquinoline-2(3H)-acetic acid

収率 60.8%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   温度heated
2. 2
   温度at reflux for 15 minutes
3. 3
   温度After cooling the precipitate
4. 4
   ろ過was collected by filtration
5. 5
   workup.DISSOLUTIONdissolved in water
6. 6
   抽出extracted with ethyl acetate
7. 7
   乾燥The extract was dried (MgSO4)
8. 8
   その他evaporated to dryness the oily residue
9. 9
   その他was triturated with hexane
10. 10
    その他The solid was recrystallized from benzene-hexane

実験手順

In a nitrogen atmosphere, a suspension of 6-chloro-1,3-dioxo-1H-benz[de]-isoquinoline-2(3H)-acetic acid (5.0 g, 17.3 mmoles, described in Example 2), 1-decanethiol (3.3 g, 3.9 ml, 19 mmoles) and anhydrous sodium carbonate (2.4 g, 17.3 mmoles) in dimethylformamide (150 ml) was stirred and heated at reflux for 15 minutes. After cooling the precipitate was collected by filtration and then dissolved in water. The solution was acidified with 2 N hydrochloric acid and extracted with ethyl acetate. The extract was dried (MgSO4) and evaporated to dryness the oily residue was triturated with hexane. The solid was recrystallized from benzene-hexane to give 4.50 g of the title product; mp 137°-140° C.; UV (MeOH) 257, 329, 343 and 382, ε=16,375, 2,849, 4,929 and 15,820, respectively; IR (CHCl3) δ2900, 1725 (inflection), 1698, 1662 cm-1 ; NMR (CDCl3) 0.85 (t, 3H, J=5), 1.25 (m, 16H), 3.1 (t, 2H, J=6.5), 4.92 (s, 2H), 8.45 (m, 3H), 9.75 (broad, 1H); Anal. Calc'd: C, 67.42%; H, 6.84%; N, 3.28%; Found: C, 67.17%; H, 6.84%; N, 3.21%.

出典