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

HRID 127930ノート

反応式

HRID 127930 の反応式
[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]

参加物

5

反応物 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 23470789HCID 23470789、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-24d1c014e33942fbb9b03058e30bb6e4
出典データセット
uspto-grants-1981_03
特許番号
US04258045

反応ノート

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