3-Amino-4-methoxybenzanilide → HCID 18626281, compound

HRID 1859669Notes

Reaction equation

HRID 1859669 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].I[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=C(C)C=C(C)C=1.O1CCCC1.C(OCC)(=O)C.[Cu]I>[N+:26]([C:22]1[CH:21]=[C:20]([NH:1][C:2]2[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:6])[CH:25]=[CH:24][CH:23]=1)([O-:28])=[O:27]

Participants

8

Reactant 3

HCID 84263-Amino-4-methoxybenzanilideHCID 11430Potassium CarbonateHCID 125741-Iodo-3-nitrobenzene

Product 1

HCID 18626281HCID 18626281, compoundYield 6.2%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 7947MesityleneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-amino-4-methoxy-N-phenyl-benzamide (2.0 g, 8 mmol), 1-iodo-3-nitrobenzene (2.5 g, 10 mmol), potassium carbonate (2.8 g, 20 mmol), and copper(I) iodide (0.4 g, 2 mmol) in mesitylene (20 mL) was stirred under an inert atmosphere and heated to reflux. After 48 hours, the mixture was allowed to cool and was then diluted with tetrahydro-furan (100 mL) and filtered through Celite. The filtrate was stripped of solvent under reduced pressure to leave an oily residue which was dissolved in ethyl acetate (250 mL) and extracted successively with 2N hydrochloric acid (2×200 mL), water, 0.5 M aqueous potassium carbonate, water, and saturated aqueous sodium chloride, then dried over MgSO4. The solution was filtered and the filtrate stripped of solvent under reduced pressure. The resulting residue was subjected to chromatography on a column of silica gel in chloroform to afford the product (0.18 g); m.p. 220-221° C. after recrystallization from acetonitrile.

Workup

  1. temperatureheated to reflux
  2. temperatureto cool
  3. filtrationfiltered through Celite
  4. customto leave an oily residue which
  5. extractionextracted successively with 2N hydrochloric acid (2×200 mL), water, 0.5 M aqueous potassium carbonate, water, and saturated aqueous sodium chloride
  6. dry with materialdried over MgSO4
  7. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-a6732ebe5c5e4caaa90e643749134cf9
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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