Potassium Carbonate → 3-{[2-(1,3-dioxolan-2-yl)ethyl]amino}-N,N-bis(3-methylbutyl)-4-nitrobenzamide

HRID 1784270Notes

Reaction equation

HRID 1784270 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:5]([N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6].[NH2:24][CH2:25][CH2:26][CH:27]1[O:31][CH2:30][CH2:29][O:28]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:28]1[CH2:29][CH2:30][O:31][CH:27]1[CH2:26][CH2:25][NH:24][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:5]([N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 798271,3-Dioxolane-2-ethylamineHCID 684471113-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide

Product 1

HCID 687931973-{[2-(1,3-dioxolan-2-yl)ethyl]amino}-N,N-bis(3-methylbutyl)-4-nitrobenzamideYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide prepared according to Example A1 (1.86 g, 1 eq), 2-(2-aminoethyl)-1,3-dioxolane (0.8 g, 1.2 eq) and potassium carbonate (1.58 g, 2 eq) in acetonitrile (150 ml) is heated under reflux for 3 hours then concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (150 ml) and water (60 ml). After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the residue by flash chromatography on silica gel (eluent: heptane/ethyl acetate 8:2 to 7:3) produces the expected compound in the form of an orange-yellow oil (2.4 g; 98% yield).

Workup

  1. customprepared
  2. temperatureis heated
  3. temperatureunder reflux for 3 hours
  4. concentrationthen concentrated under reduced pressure at 40° C
  5. extractionAfter decantation and extractions
  6. washthe combined organic phases are washed with salt water
  7. dry with materialdried over Na2SO4
  8. concentrationthen concentrated under reduced pressure at 40° C
  9. customPurification of the residue by flash chromatography on silica gel (eluent: heptane/ethyl acetate 8:2 to 7:3)

Sources & evidence

ORD record
ord-f7774b1580534680a4b78f29a99fddb0
Source dataset
uspto-grants-2009_03
Patent number
US07501524B2

Reaction notes

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