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

HRID 962864노트

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HRID 962864 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 218131431-(4-Aminobenzoyl)azepan-2-one수율 68%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
0 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-001a39d52d914a51ac2d309f21122036
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760143

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