Pyridine → HCID 18988726, compound

HRID 2396160Notes

Reaction equation

HRID 2396160 reaction equation
[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:9]([C:12]1[CH:37]=[CH:36][C:15]([O:16][C:17]2[CH:18]=[C:19]([CH:23]=[C:24]([O:26][C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=3)[CH:25]=2)[C:20](Cl)=[O:21])=[CH:14][CH:13]=1)([O-:11])=[O:10].N1C=CC=CC=1>C1C=CC=CC=1>[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([O:16][C:17]2[CH:18]=[C:19]([CH:23]=[C:24]([O:26][C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=3)[CH:25]=2)[C:20]([CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:1]2=[O:8])=[O:21])=[CH:36][CH:37]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7768CaprolactamHCID 189887293,5-Bis(4-nitrophenoxy)benzoyl chloride

Product 1

HCID 18988726HCID 18988726, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of ε-caprolactam (14.82 g, 0.131 mol) in 400 ml of benzene is added to the above reactor containing 0.131 mol of 3,5-bis(4-nitrophenoxy)benzoyl chloride. The mixture is heated to 80°-90° C., and after all the reactants are dissolved, 150 ml of pyridine is added. The solution is stirred at 90° C. for 3 hours and the pyridine/acid chloride salt removed by filtration, the filtrate being kept in a freezer. White crystals formed from the filtrate are collected by filtration and dried. In order to remove traces of the 3,5-bis(4-nitrophenoxy)benzoic acid, the product is further purified by chromatography using silica gel as filler and ethyl acetate as eluate to yield 65 percent of white crystals: mp 157°-158° C.

Workup

  1. temperatureThe mixture is heated to 80°-90° C.
  2. dissolutionafter all the reactants are dissolved
  3. customthe pyridine/acid chloride salt removed by filtration
  4. customWhite crystals formed from the filtrate
  5. filtrationare collected by filtration
  6. customdried
  7. customIn order to remove traces of the 3,5-bis(4-nitrophenoxy)benzoic acid
  8. customthe product is further purified by chromatography

Sources & evidence

ORD record
ord-55670efed41c489c908fb06f8d21546d
Source dataset
uspto-grants-1996_02
Patent number
US05491200

Reaction notes

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