P-Anisidine → N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(2-methoxyphenyl)benzoyl]-4-methoxyaniline

HRID 1245227Notes

Reaction equation

HRID 1245227 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:31])[C:5]([CH3:30])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:17]([CH:21]=2)[C:18]([OH:20])=O)[C:7](=[O:11])[C:8]=1[O:9][CH3:10].[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=1.C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[C:4](=[O:31])[C:5]([CH3:30])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:17]([CH:21]=2)[C:18]([NH:40][C:37]2[CH:38]=[CH:39][C:34]([O:33][CH3:32])=[CH:35][CH:36]=2)=[O:20])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 219191365-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(2-methoxyphenyl)benzoic acid

Product 1

HCID 21919149N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(2-methoxyphenyl)benzoyl]-4-methoxyanilineYield 46.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(2-methoxyphenyl) benzoic acid (66 mg, 0.1563 mmol) was dissolved in methylene chloride (5 ml), then p-anisidine (38 mg, 0.3089 mmol), triethylamine (47 mg, 0.4653 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (53 mg, 0.3136 mmol) were added thereto at room temperature and the mixture was stirred at room temperature for 16 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and dried and the solvent was evaporated therefrom. The residue was purified by preparative thin layer silica gel (hexane:ethyl acetate=1:1) to give the title compound (38 mg, 0.0721 mmol, 46%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was evaporated
  5. customThe residue was purified by preparative thin layer silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-6d6f9872052a487087b4aa13b63f19cd
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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