Реакция #42276

Уравнение реакции

Carbonyl diimidazole

mono-methyl 5-nitro-isophthalate

Dipropylamine

→

title compound

Methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe reaction mixture is then stirred for 4 hours
2. 2
   ДругоеThe solvent is removed under reduced pressure
3. 3
   Другоеthe mixture is partitioned between ethyl acetate and water
4. 4
   ДругоеThe organic phase is separated
5. 5
   Промывкаwashed with saline
6. 6
   Сушкаdried over anhydrous sodium sulfate
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated

Методика

Carbonyl diimidazole (3.90 g, 24.0 mmol) is added to a mixture of mono-methyl 5-nitro-isophthalate (XXVIII, 4.50 g, 20.0 mmol) in dry THF (50 mL). The mixture is stirred for 0.5 hours. Dipropylamine (3.28 mL, 24.0 mmol) is added slowly to the mixture. The reaction mixture is then stirred for 4 hours. The solvent is removed under reduced pressure and the mixture is partitioned between ethyl acetate and water. The organic phase is separated and washed with saline, dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography (silica gel; ethyl acetate/hexanes, 15/85) gives the title compound, NMR (300 MHz, CDCl3) delta 8.88, 8.41, 8.35, 4.00, 3.48, 3.15, 1.72, 1.57, 1.00 and 0.77; MS (ESI+) for C15H20N2O5 m/z (M+H)+=309.2.

Источник