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

HRID 1247547Notes

Reaction equation

HRID 1247547 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-oneYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A 3-liter three-necked flask was charged with 144 g (1.27 moles) of ε-caprolactam, 2 L of toluene, and 1 L of pyridine. The mixture was stirred at 0° C. under nitrogen, to which was then added 256.5 g (1.27 moles) of p-sulfinylaminobenzoyl chloride. The mixture was slowly stirred until the temperature reached room temperature and then reacted for 14 hours. A deposited pyridine hydrochloride was filtered off, and the filtrate was washed twice with a 5% sodium hydrogencarbonate aqueous solution. A white residue obtained by distilling off the solvent of the organic phase was recrystallized twice from ethyl acetate to obtain N-(p-aminobenzoyl)caprolactam in a percent yield of 68%.

Workup

  1. stirringThe mixture was slowly stirred until the temperature
  2. customreached room temperature
  3. customreacted for 14 hours
  4. filtrationA deposited pyridine hydrochloride was filtered off
  5. washthe filtrate was washed twice with a 5% sodium hydrogencarbonate aqueous solution
  6. customA white residue obtained
  7. distillationby distilling off the solvent of the organic phase
  8. customwas recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-2eb2bab3ee914019882f814567e55fde
Source dataset
uspto-grants-2006_10
Patent number
US07129314B2

Reaction notes

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