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

HRID 962864Notes

Reaction equation

HRID 962864 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 three liter-volume three-necked flask was charged with 144 g (1.27 mol) of caprolactam, 2 liters of toluene and 1 liter of pyridine, and the content was stirred at 0° C. under a nitrogen gas atmosphere. Then 256.5 g (1.27 mol) of p-sulfinylaminobenzoyl chloride, synthesized in Synthesis Example 1, was added into the flask, and the mixture was gently stirred until the temperature reached room temperature. Thereafter the content was stirred for 14 hours to conduct a reaction. Pyridine hydrochloride, thus precipitated, was filtered and the filtrate was washed twice with aqueous 5% sodium hydrogencarbonate. The solvent was distilled off under a reduced pressure from the organic phase to afford a white residue. The white residue was twice recrystallized from ethyl acetate to give N-(p-aminobenzoyl)caprolactam having a melting point of 156°-158° C. in a yield of 68%.

Workup

  1. additionwas added into the flask
  2. stirringthe mixture was gently stirred until the temperature
  3. customreached room temperature
  4. stirringThereafter the content was stirred for 14 hours
  5. customa reaction
  6. customPyridine hydrochloride, thus precipitated
  7. filtrationwas filtered
  8. washthe filtrate was washed twice with aqueous 5% sodium hydrogencarbonate
  9. distillationThe solvent was distilled off under a reduced pressure from the organic phase
  10. customto afford a white residue
  11. customThe white residue was twice recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-001a39d52d914a51ac2d309f21122036
Source dataset
uspto-grants-1998_06
Patent number
US05760143

Reaction notes

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