Sodium Chloride → Pyridine-3-sulfonyl chloride

HRID 268926

反応式

HRID 268926 の反応式
[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

参加物

7

反応物 5

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

生成物 1

HCID 3164136Pyridine-3-sulfonyl chloride収率 94.3%

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒

実験手順

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)+].

後処理

  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

出典と根拠

ORDレコード
ord-f04bdb6b900a43cb9eb113fee6b6c913
出典データセット
uspto-grants-2008_11
特許番号
US07446113B2

関連ノート

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