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

HRID 1387518Notes

Reaction equation

HRID 1387518 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 tetrahydrofuran (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-cebeb705397f4561863e5359cb58d4a5
Source dataset
uspto-grants-2001_07
Patent number
US06268387B1

Reaction notes

Loading…