Triethylamine → HCID 22054136, compound

HRID 1830346Notes

Reaction equation

HRID 1830346 reaction equation
[Cl-].ClC1N(C)CC[NH+]1C.[NH2:10][C:11]1[C:12]([Cl:17])=[N:13][CH:14]=[CH:15][CH:16]=1.C(N(CC)CC)C.[CH3:25][O:26][C:27]1[C:28](=[O:51])[C:29]([CH3:50])=[C:30]([CH2:36][C:37]2[CH:45]=[CH:44][C:40]([C:41](O)=[O:42])=[C:39]([O:46][C:47](=[O:49])[CH3:48])[CH:38]=2)[C:31](=[O:35])[C:32]=1[O:33][CH3:34]>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:17][C:12]1[C:11]([NH:10][C:41](=[O:42])[C:40]2[CH:44]=[CH:45][C:37]([CH2:36][C:30]3[C:31](=[O:35])[C:32]([O:33][CH3:34])=[C:27]([O:26][CH3:25])[C:28](=[O:51])[C:29]=3[CH3:50])=[CH:38][C:39]=2[O:46][C:47](=[O:49])[CH3:48])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 805282-Chloro-3-pyridylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 22054194HCID 22054194, compound

Product 1

HCID 22054136HCID 22054136, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-1,3-dimethylimidazolinium chloride (89 mg, 0.524 mmol), 3-amino-2-chloropyridine (51 mg, 0.390 mmol) and triethylamine (53 mg, 0.524 mmol) were added to a methylene chloride solution (10 ml) of 4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (98 mg, 0.120 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 (hexand:ethyl acetate=3:1) to obtain the titled compound (29 mg, 0.060 mmol, 23%).

Workup

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

Sources & evidence

ORD record
ord-5fccd15d505444298f503cb6a1857803
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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