Triethylamine → HCID 22054224, compound

HRID 1830415Notes

Reaction equation

HRID 1830415 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=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[C:37]([O:45][C:46](=[O:48])[CH3:47])=[C:38]([CH:42]=[CH:43][CH:44]=2)[C:39](O)=[O:40])[C:30](=[O:34])[C:31]=1[O:32][CH3:33]>C(Cl)Cl>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:39](=[O:40])[C:38]2[CH:42]=[CH:43][CH:44]=[C:36]([CH2:35][C:29]3[C:30](=[O:34])[C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[C:27](=[O:50])[C:28]=3[CH3:49])[C:37]=2[O:45][C:46](=[O:48])[CH3:47])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 22054160HCID 22054160, compound

Product 1

HCID 22054224HCID 22054224, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Aminopyridine (0.076 g, 0.802 mmol), triethylamine (0.081 g, 0.802 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.136 g, 0.802 mmol) were added to a methylene chloride solution (100 ml) of 3-(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 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 (chloroform:methanol=10:1) to obtain the titled compound (0.100 g, 0.222 mmol, 41%).

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 (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-f561ea2c7f4743ad8286f2ba69aef90b
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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