Benzene → HCID 86749248, compound

HRID 2396165Notes

Reaction equation

HRID 2396165 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]1(=[O:20])[NH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C1C=CC=CC=1>N1C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:13]2=[O:20])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 241BenzeneHCID 7768CaprolactamHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 86749248HCID 86749248, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A mixture of 4-nitrobenzoyl chloride (50.16 g, 0.27 mol), freshly distilled ε-caprolactam (30.59 g, 0.27 mol), and 500 ml of benzene are 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. and after all the solids are dissolved, 160 ml of pyridine is added. White pyridine salts form immediately, the reaction solution being kept at 90°-100° C. for 1 hour. The pyridine salts are removed by filtration, and the solvent is separated from the filtrate under reduced pressure. The residue is washed with a 5 percent NaHCO3 aqueous solution and with distilled water several times before being dried. The product is then recrystallized from a mixture of ethyl acetate and hexane to obtain 67 g (95 percent) of white crystals: mp 105°-106° C.

Workup

  1. customequipped 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. customThe pyridine salts are removed by filtration
  5. customthe solvent is separated from the filtrate under reduced pressure
  6. washThe residue is washed with a 5 percent NaHCO3 aqueous solution and with distilled water several times
  7. custombefore being dried
  8. customThe product is then recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-ff337b0319814f64bf210857806b9a0e
Source dataset
uspto-grants-1996_02
Patent number
US05491200

Reaction notes

Loading…