反応 #42275

反応方程式

urea hydrogen peroxide

3-cyano-5-[(dipropylamino)carbonyl]benzoic acid

3-Cyano-5-[(dipropylamino)carbonyl]benzoic acid

potassium carbonate

acetone

urea hydrogen peroxide

urea hydrogen peroxide

→

title compound

3-(Aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoic acid

溶媒

Water

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture is stirred for 15 hours at 20-25 degrees C
2. 2
   workup.STIRRINGafter stirring for another 3 hours
3. 3
   その他After a total of 39 hours
4. 4
   その他the acetone is removed under reduced pressure
5. 5
   抽出The mixture is extracted with dichloromethane
6. 6
   その他the organic layer is separated
7. 7
   洗浄washed with hydrochloric acid (0.5 N)
8. 8
   乾燥the organic phase is dried with anhydrous magnesium sulfate to a solid
9. 9
   その他The solid is crystallized from dichloromethane/hexane/methanol

実験手順

A mixture of 3-cyano-5-[(dipropylamino)carbonyl]benzoic acid (IX/XXXII, PREPARATION 7, 0.602 g, 2.19 mmol), potassium carbonate (0.212 g, 1.53 mmol), and acetone (2.5 mL) is stirred at 20-25 degrees C. Water (2.5 mL) and urea-hydrogen peroxide adduct (0.825 g, 8.78 mmol) are added and the mixture is stirred for 15 hours at 20-25 degrees C., at which time additional urea-hydrogen peroxide adduct (0.204 g) is added; after stirring for another 3 hours, an additional 0.205 g of urea-hydrogen peroxide is added. After a total of 39 hours has elapsed, the acetone is removed under reduced pressure and the residue is acidified with hydrochloric acid (3N) to pH=2-4. The mixture is extracted with dichloromethane, the organic layer is separated and washed with hydrochloric acid (0.5 N), and the organic phase is dried with anhydrous magnesium sulfate to a solid. The solid is crystallized from dichloromethane/hexane/methanol to give the title compound, MS (ESI+) for C15H20N2O4 m/z (M+H)+=293.2.

出典