Potassium Carbonate → HCID 68793197, compound

HRID 1161003Notes

Reaction equation

HRID 1161003 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 68793197HCID 68793197, compoundYield 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-d3e9e69df2234b9db7472e03669b61a9
Source dataset
uspto-grants-2010_10
Patent number
US07816539B2

Reaction notes

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