Reaction #79476

Reaction equation

dimethyl formamide

1,10-Decanediol

isatoic anhydride

1,4-diazabicyclo[2.2.2]octane

→

1,10-decanediyl dianthranilate

Yield 29.0%

Solvents

methanol

water

Conditions

Workup

1. 1
   TemperatureThe mixture was then cooled to room temperature
2. 2
   Otherformed crystals
3. 3
   Filtrationwas filtered
4. 4
   WashThe solid was washed with 4×200 milliliter portions of a 75:25 (volume:volume) mixture of methanol/water
5. 5
   Otherwas dried

Procedure

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-NMR. The melting point of this product as measured by Differential Scanning Calorimetry was 77° C.

Source