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

HRID 1987738Notes

Reaction equation

HRID 1987738 reaction equation
C(C1NC=CN=1)(C1NC=CN=1)=O.[N+:13]([C:16]1[CH:17]=[C:18]([C:26]([O-:28])=O)[CH:19]=[C:20]([CH:25]=1)[C:21]([O:23][CH3:24])=[O:22])([O-:15])=[O:14].[CH2:29]([NH:32][CH2:33][CH2:34][CH3:35])[CH2:30][CH3:31]>C1COCC1>[CH2:29]([N:32]([CH2:33][CH2:34][CH3:35])[C:26]([C:18]1[CH:19]=[C:20]([CH:25]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=1)[C:21]([O:23][CH3:24])=[O:22])=[O:28])[CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 6931682Monomethyl-5-nitroisophthalate

Product 1

HCID 690570Methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. stirringThe reaction mixture is then stirred for 4 hours
  2. customThe solvent is removed under reduced pressure
  3. customthe mixture is partitioned between ethyl acetate and water
  4. customThe organic phase is separated
  5. washwashed with saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ed89edafcad24bd28fb732cf4a5eea2e
Source dataset
uspto-grants-2009_06
Patent number
US07553831B2

Reaction notes

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