Sodium Chloride → Pyridine-3-sulfonyl chloride

HRID 268926

반응식

HRID 268926 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([OH:10])(=O)=[O:8])[CH:2]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:12].P(Cl)(Cl)(Cl)=O.C([O-])(O)=O.[Na+].[Na+].[Cl-]>COC(C)(C)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([Cl:12])(=[O:10])=[O:8])[CH:2]=1

참가 물질

7

반응물 5

HCID 5234Sodium ChlorideHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acidHCID 516892Sodium Bicarbonate

생성물 1

HCID 3164136Pyridine-3-sulfonyl chloride수율 94.3%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

실험 절차

A mixture of pyridine-3-sulfonic acid (10.3 g, 64.8 mmol), phosphorus pentachloride (20.82 g, 100 mmol) and phosphorus oxychloride (10 mL, 109 mmol) was heated to reflux for 3 h (according to J. Org. Chem. 1989, 54(2), 389.). Evaporated to dryness to give a yellow solid, dissolved in ice water and methyl-tert-butyl ether, added cautiously sat. NaHCO3-sol. until neutralized, saturated with solid NaCl, separated phases, dried organic layer over Na2SO4. Removal of the solvent in vacuum to give the title compound as an orange liquid (10.85 g, 94%). MS (ISP) 178.1 [(M+H)+] and 180.0 [(M+2+H)+].

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 3 h (according to J. Org. Chem. 1989, 54(2), 389.)
  3. customEvaporated to dryness
  4. customto give a yellow solid
  5. customseparated phases, dried organic layer over Na2SO4
  6. customRemoval of the solvent in vacuum

출처 및 근거

ORD 기록
ord-f04bdb6b900a43cb9eb113fee6b6c913
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446113B2

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