Triethylamine → HCID 22054124, compound

HRID 1830366Notes

Reaction equation

HRID 1830366 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.[CH3:24][O:25][C:26]1[C:27](=[O:50])[C:28]([CH3:49])=[C:29]([CH2:35][C:36]2[CH:37]=[CH:38][C:39]([O:45][C:46](=[O:48])[CH3:47])=[C:40]([CH:44]=2)[C:41](O)=[O:42])[C:30](=[O:34])[C:31]=1[O:32][CH3:33]>C(Cl)Cl>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:41](=[O:42])[C:40]1[CH:44]=[C:36]([CH2:35][C:29]2[C:30](=[O:34])[C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[C:27](=[O:50])[C:28]=2[CH3:49])[CH:37]=[CH:38][C:39]=1[O:45][C:46](=[O:48])[CH3:47]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 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 22054124HCID 22054124, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Aminopyridine (0.282 g, 3.000 mmol), triethylamine (0.304 g, 3.000 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.507 g, 3.000 mmol) were added to a methylene chloride solution (50 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.374 g, 1.000 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 (hexand:ethyl acetate=1:1) and then recrystallized from ether to obtain the titled compound (0.140 g, 0.311 mmol, 31%).

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 (hexand:ethyl acetate=1:1)
  6. customrecrystallized from ether

Sources & evidence

ORD record
ord-4bf628f425054545a49356433393fa7d
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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