반응 #42276

반응 방정식

Carbonyl diimidazole

mono-methyl 5-nitro-isophthalate

Dipropylamine

→

title compound

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

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture is then stirred for 4 hours
2. 2
   기타The solvent is removed under reduced pressure
3. 3
   기타the mixture is partitioned between ethyl acetate and water
4. 4
   기타The organic phase is separated
5. 5
   세척washed with saline
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated

실험 절차

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.

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