Triethylamine → N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-2,6-dichloro-4-trifluoromethoxyaniline

HRID 1830402Notes

Reaction equation

HRID 1830402 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([Cl:14])[C:3]=1[NH2:4].C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.[CH3:31][O:32][C:33]1[C:34](=[O:57])[C:35]([CH3:56])=[C:36]([CH2:42][C:43]2[CH:44]=[CH:45][C:46]([O:52]C(=O)C)=[C:47]([CH:51]=2)[C:48](O)=[O:49])[C:37](=[O:41])[C:38]=1[O:39][CH3:40]>C(Cl)Cl>[CH3:31][O:32][C:33]1[C:34](=[O:57])[C:35]([CH3:56])=[C:36]([CH2:42][C:43]2[CH:44]=[CH:45][C:46]([OH:52])=[C:47]([CH:51]=2)[C:48]([NH:4][C:3]2[C:2]([Cl:1])=[CH:8][C:7]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=2[Cl:14])=[O:49])[C:37](=[O:41])[C:38]=1[O:39][CH3:40]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6882472,6-Dichloro-4-(trifluoromethoxy)anilineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 220542715-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic Acid

Product 1

HCID 22054263N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzoyl]-2,6-dichloro-4-trifluoromethoxyanilineYield 33.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-Dichloro-4-trifluoromethoxyaniline (0.395 g, 1.604 mmol), triethylamine (0.162 g, 1.604 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.271 g, 1.604 mmol) were added to a methylene chloride solution (100 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.200 g, 0.535 mmol) and the resulting solution was stirred at room temperature for 10 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (ethyl acetate:hexane=1:2) and then recrystallized from ether to obtain the titled compound (0.099 g, 0.177 mmol, 33%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe obtained residue was purified by preparative thin-layer chromatography (ethyl acetate:hexane=1:2)
  6. customrecrystallized from ether

Sources & evidence

ORD record
ord-842065accae94462937dcc89853b08e2
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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