Benzene → HCID 18988728, compound

HRID 2396161Notes

Reaction equation

HRID 2396161 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[C:16]1(=[O:23])[NH:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C1C=CC=CC=1>N1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7]([CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:16]1=[O:23])=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 241BenzeneHCID 74323,5-Dinitrobenzoyl chlorideHCID 7768Caprolactam

Product 1

HCID 18988728HCID 18988728, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 3,5-dinitrobenzoyl chloride (50.00 g, 0.22 mol), freshly distilled ε-caprolactam (24.54 g, 0.22 mol) and 500 ml of benzene is added to a 1L, three-necked, round-bottom flask equipped with an overhead stirrer, condenser and a nitrogen inlet tube. The solution is heated to 90°-100° C. After all the solids are dissolved, 165 ml of pyridine is added. White pyridine salts form immediately, and the reaction solution is kept at 90°-100° C. for 1 hour before removing the pyridine salts by filtration. The solvent is removed from the filtrate under reduced pressure and the residue is washed by a 5 percent NaHCO3 aqueous solution and distilled water several times before being dried. The product is recrystallized from a mixture of ethyl acetate and hexane to obtain 45 g (68 percent) of white crystals: mp 126°-126.5° .

Workup

  1. customthree-necked, round-bottom flask equipped with an overhead stirrer, condenser and a nitrogen inlet tube
  2. temperatureThe solution is heated to 90°-100° C
  3. dissolutionAfter all the solids are dissolved
  4. custombefore removing the pyridine salts
  5. filtrationby filtration
  6. customThe solvent is removed from the filtrate under reduced pressure
  7. washthe residue is washed by a 5 percent NaHCO3 aqueous solution
  8. distillationdistilled water several times
  9. custombefore being dried
  10. customThe product is recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-34f53e26d19f403d997879b9556b8989
Source dataset
uspto-grants-1996_02
Patent number
US05491200

Reaction notes

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