反応 #1456318

反応方程式

dimethyl formamide

1,10-Decanediol

isatoic anhydride

1,4-diazabicyclo[2.2.2]octane

→

1,10-decanediyl dianthranilate

収率 29.0%

溶媒

methanol

water

反応条件

後処理

1. 1
   温度The mixture was then cooled to room temperature
2. 2
   その他formed crystals
3. 3
   ろ過was filtered
4. 4
   洗浄The solid was washed with 4×200 milliliter portions of a 75:25 (volume:volume) mixture of methanol/water
5. 5
   その他was dried

実験手順

1,10-Decanediol (174 grams, 1.0 mol), isatoic anhydride (367 g, 2.25 mol; obtained from Sigma-Aldrich), 1,4-diazabicyclo[2.2.2]octane (22.4 grams, 0.20 mol), and dimethyl formamide (500 milliliters) were combined in 2 liter beaker and the resulting mixture was heated at 120° C. for 1 hour. The mixture was then cooled to room temperature and was treated first with methanol (1,500 milliliters) and then with water (500 milliliters). The solution turned cloudy, and then formed crystals. The crystal suspension was stirred for 2 hours at room temperature, and then was filtered. The solid was washed with 4×200 milliliter portions of a 75:25 (volume:volume) mixture of methanol/water, and then was dried to give 1,10-decanediyl dianthranilate as a light beige solid (119 grams, 29 percent yield). The product was adjudged to be highly pure (greater than 98 percent) by 1H-NMR1 The melting point of this product as measured by Differential Scanning Calorimetry was 77° C.

出典