Triethylamine → N-[3-(3.4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoyl]-4-trifluoromethylaniline

HRID 1245196Notes

Reaction equation

HRID 1245196 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:31])=[C:5]([C:22]([O:29][CH3:30])=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[C:8]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](O)=[O:11].[F:32][C:33]([F:42])([F:41])[C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1.C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([CH3:31])=[C:5]([C:22]([O:29][CH3:30])=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[C:8]([C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([NH:38][C:37]1[CH:39]=[CH:40][C:34]([C:33]([F:41])([F:42])[F:32])=[CH:35][CH:36]=1)=[O:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 99644-(Trifluoromethyl)anilineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 219191873-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoic acid

Product 1

HCID 21919142N-[3-(3.4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoyl]-4-trifluoromethylanilineYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoic acid (18 mg, 0.0424 mmol) in methylene chloride (3 ml) were added 4-trifluoromethylaniline (10.2 mg, 0.0633 mmol), triethylamine (8.6 mg, 0.0851 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (21.5 mg, 0.1272 mmol) followed by stirring at room temperature for 16 hours. The reaction solution was washed with water and dried and the solvent was evaporated therefrom. The residue was purified by preparative thin layer chromatography (methylene chloride:methanol=95:5) to give the title compound (17 mg, 0.0300 mmol, 71%).

Workup

  1. washThe reaction solution was washed with water
  2. customdried
  3. customthe solvent was evaporated
  4. customThe residue was purified by preparative thin layer chromatography (methylene chloride:methanol=95:5)

Sources & evidence

ORD record
ord-3806d92e83c74141a84ba5e06afde034
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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