Triethylamine → N-[4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-phenylbenzoyl]-4-trifluoromethyl-Aniline

HRID 1245206Notes

Reaction equation

HRID 1245206 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:29])[C:5]([CH3:28])=[C:6]([CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:14]=2)[C:7](=[O:11])[C:8]=1[O:9][CH3:10].[F:30][C:31]([F:40])([F:39])[C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=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:29])[C:5]([CH3:28])=[C:6]([CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:36][C:35]3[CH:37]=[CH:38][C:32]([C:31]([F:39])([F:40])[F:30])=[CH:33][CH:34]=3)=[O:18])=[C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:14]=2)[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 99644-(Trifluoromethyl)anilineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 219191464-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-phenylbenzoic acid

Product 1

HCID 21919206N-[4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-phenylbenzoyl]-4-trifluoromethyl-AnilineYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-phenylbenzoic acid (16 mg, 0.0408 mmol) was dissolved in methylene chloride (3 ml), then 4-trifluoromethylaniline (13 mg, 0.0807 mmol), triethylamine (8.2 mg, 0.0811 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (21 mg, 0.1242 mmol) were added thereto and the mixture was stirred 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 chromatography (hexane:ethyl acetate=1:1) to give the title compound (8 mg, 0.0149 mmol, 37%).

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 chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3c4b9315c32d44c193fad385637eeb28
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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