Triethylamine → HCID 22054135, compound

HRID 1830350Notes

Reaction equation

HRID 1830350 reaction equation
[Cl-].ClC1N(C)CC[NH+]1C.[NH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.C(N(CC)CC)C.[CH3:24][O:25][C:26]1[C:27](=[O:50])[C:28]([CH3:49])=[C:29]([CH2:35][C:36]2[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[C:38]([O:45][C:46](=[O:48])[CH3:47])[CH:37]=2)[C:30](=[O:34])[C:31]=1[O:32][CH3:33]>C(Cl)(Cl)Cl.C(Cl)Cl>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([NH:10][C:40](=[O:41])[C:39]2[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])=[CH:37][C:38]=2[O:45][C:46](=[O:48])[CH3:47])[CH:12]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 22054194HCID 22054194, compound

Product 1

HCID 22054135HCID 22054135, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-1,3-dimethylimidazolinium chloride (39 mg, 0.23 mmol), 3-aminopyridine (21 mg, 0.23 mmol) and triethylamine (23 mg, 0.23 mmol) were added to a methylene chloride solution (5 ml) of 4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (57 mg, 0.152 mmol) in a nitrogen atmosphere and the resulting solution was stirred all the night through. The reaction solution was diluted with chloroform, then washed with water and dried, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography (benzene:acetone=3:1) to obtain the titled compound (12 mg, 0.027 mmol, 18%).

Workup

  1. washwashed with water
  2. customdried
  3. customthe solvent was removed by distillation
  4. customThe residue was purified by silica gel column chromatography (benzene:acetone=3:1)

Sources & evidence

ORD record
ord-d9c6e2df89bd4542ad276e8480ecba79
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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