Triethylamine → HCID 22054356, compound

HRID 1830396Notes

Reaction equation

HRID 1830396 reaction equation
[NH2:1][C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.[CH3:25][O:26][C:27]1[C:28](=[O:51])[C:29]([CH3:50])=[C:30]([CH2:36][C:37]2[CH:38]=[CH:39][C:40]([O:46][C:47](=[O:49])[CH3:48])=[C:41]([CH:45]=2)[C:42](O)=[O:43])[C:31](=[O:35])[C:32]=1[O:33][CH3:34]>C(Cl)Cl>[Cl:8][C:3]1[C:2]([NH:1][C:42](=[O:43])[C:41]2[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]=[CH:39][C:40]=2[O:46][C:47](=[O:49])[CH3:48])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 805282-Chloro-3-pyridylamineHCID 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 22054356HCID 22054356, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-2-chloropyridine (0.206 g, 1.604 mmol), triethylamine (0.162 g, 1.604 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.271 g, 1.604 mmol) were added to a methylene chloride solution (100 ml) of 5-(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 10 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 (ethyl acetate:hexane=1:1) to obtain the titled compound (0.140 g, 0.289 mmol, 54%).

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 (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-937f732cafdc473d8043f5d03250d75c
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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