P-Anisidine → HCID 22054223, compound

HRID 1830227Notes

Reaction equation

HRID 1830227 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.[CH3:26][O:27][C:28]1[C:29]([CH3:58])=[C:30]([C:49]([O:56][CH3:57])=[C:50]([O:54][CH3:55])[C:51]=1[O:52][CH3:53])[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[C:36]([CH:40]=1)[C:37](O)=[O:38]>C(Cl)Cl>[CH3:26][O:27][C:28]1[C:29]([CH3:58])=[C:30]([C:49]([O:56][CH3:57])=[C:50]([O:54][CH3:55])[C:51]=1[O:52][CH3:53])[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[C:36]([CH:40]=1)[C:37]([NH:7][C:6]1[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:38]

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 21919197HCID 21919197, compound

Product 1

HCID 22054223HCID 22054223, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Methoxyaniline (0.250 g, 2.03 mmol), triethylamine (0.206 g, 2.03 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.344 g, 2.03 mmol) were added to a methylene chloride solution (40 ml) of 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic acid (0.460 g, 1.02 mmol) and the resulting solution was stirred at room temperature for 12 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 recrystallized from ether to obtain the titled compound (0.211 g, 0.379 mmol, 37%).

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-c74834ed9a5e4bbfbd073fdffd71114c
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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