Triethylamine → HCID 22054157, compound

HRID 1830345Notes

Reaction equation

HRID 1830345 reaction equation
[Cl-].ClC1N(C)CC[NH+]1C.[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[N: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(=O)C)[CH:38]=2)[C:31](=[O:35])[C:32]=1[O:33][CH3:34]>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:17][C:14]1[N:15]=[CH:16][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[OH:46])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 793055-Amino-2-chloropyridineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 22054194HCID 22054194, compound

Product 1

HCID 22054157HCID 22054157, compoundYield 17.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-1,3-dimethylimidazolinium chloride (61 mg, 0.361 mmol), 5-amino-2-chloropyridine (46 mg, 0.361 mmol) and triethylamine (36 mg, 0.361 mmol) were added to a methylene chloride solution (3 ml) of 4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (45 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 (10 mg, 0.021 mmol, 17%).

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-f6e635f554b94602b86f9fcad11affef
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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