3-Amino-4-methoxybenzanilide → HCID 18626298, compound

HRID 1859670Notes

Reaction equation

HRID 1859670 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].[Cl:19][C:20]1[CH:21]=[C:22](I)[CH:23]=[C:24]([Cl:26])[CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.[Cu]I>[Cl:19][C:20]1[CH:21]=[C:22]([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:23]=[C:24]([Cl:26])[CH:25]=1

Participants

6

Reactant 3

HCID 84263-Amino-4-methoxybenzanilideHCID 11430Potassium CarbonateHCID 764241,3-Dichloro-5-iodobenzene

Product 1

HCID 18626298HCID 18626298, compoundYield 9.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolvent

Procedure

Prepared according to the procedure of Example 33 using 3-amino-4-methoxy-N-phenyl-benzamide (2.0 g, 8.3 mmol), 3,5-dichloroiodobenzene (4.5 g, 16.5 mmol), potassium carbonate (2.9 g, 21.0 mmol), and copper(I) iodide (0.5 g, 2.6 mmol) to give a gummy residue which was subjected to chromatography on a column of silica gel in dichloromethane to afford the product (0.3 g); m.p. 207-208° C. after recrystallization from ethanol.

Workup

  1. customPrepared
  2. customto give a gummy residue which

Sources & evidence

ORD record
ord-6c042cf560e446ddbf3b0448a124488e
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

Loading…