Toluene → 1-(4-Aminobenzoyl)azepan-2-one

HRID 369416Notes

Reaction equation

HRID 369416 reaction equation
[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC=CC=1.S(=[N:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)=O>N1C=CC=CC=1>[NH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([N:7]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]2=[O:8])=[O:24])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7768CaprolactamHCID 12238912Benzoyl chloride, 4-(sulfinylamino)-

Product 1

HCID 218131431-(4-Aminobenzoyl)azepan-2-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into a 3000 mL three-neck reactor were charged caprolactam (150 g, 0.703 mol), toluene (1300 mL), and pyridine (680 mL); the reactor was then purged with nitrogen. Under ice bath, p-sulfinylaminobenzoyl chloride (147.1 g, 0.730 mol) was added with stirring to the above mixture. After removing the ice-bath, the reaction mixture was stirred at room temperature for 14 hours. After this, pyridine chloride was removed by filtration and the filtrate was washed with 5% sodium bicarbonate solution two times, and then concentrated to remove the solvent. The residue was recrystallized from ethyl acetate to give N-(p-aminobenzoyl)caprolactam, a polymerizable lactam monomer.

Workup

  1. customthe reactor was then purged with nitrogen
  2. customAfter removing the ice-bath
  3. stirringthe reaction mixture was stirred at room temperature for 14 hours
  4. customAfter this, pyridine chloride was removed by filtration
  5. washthe filtrate was washed with 5% sodium bicarbonate solution two times
  6. concentrationconcentrated
  7. customto remove the solvent
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-79558ddbc7d841e0bbd086cf6ee67dd9
Source dataset
uspto-grants-2000_10
Patent number
US06136908

Reaction notes

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