Pyridine → N-{4-[(3-Chloropropyl)sulfanyl]phenyl}acetamide

HRID 127930노트

반응식

HRID 127930 반응식
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH2:14]O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.S(Cl)([Cl:24])=O>C(Cl)Cl>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH2:14][Cl:24])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 23470789HCID 23470789, 화합물

생성물 1

HCID 14005891N-{4-[(3-Chloropropyl)sulfanyl]phenyl}acetamide수율 57.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred suspension of 5.62 g (0.025 mole) of 3-(4'-acetamidophenylthio)propanol in 25 ml of methylene chloride and 2.03 ml of pyridine (0.025 mole) is added 3.7 g of thionyl chloride (0.031 mole) in 10 ml of methylene chloride. After the exothermic reaction subsides, the mixture is heated at reflux for 0.5 hr. The reaction mixture is poured into 100 ml of ice-water with stirring. The organic layer is separated, dried and concentrated to a dark red solid. Extraction of the latter with ether in a Soxlet apparatus yields 3.5 g of 3-(p-acetamidophenylthio)propyl chloride having the correct IR and NMR spectra.

후처리

  1. customAfter the exothermic reaction subsides
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 0.5 hr
  4. customThe organic layer is separated
  5. customdried
  6. concentrationconcentrated to a dark red solid
  7. extractionExtraction of the latter with ether in a Soxlet apparatus

출처 및 근거

ORD 기록
ord-24d1c014e33942fbb9b03058e30bb6e4
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04258045

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