2-Aminopyridine → 6-Aminopyridine-3-sulfonyl chloride

HRID 1173091ノート

反応式

HRID 1173091 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:8][S:9](O)(=[O:11])=[O:10].S(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([S:9]([Cl:8])(=[O:11])=[O:10])=[CH:6][CH:7]=1

参加物

5

反応物 4

HCID 104392-AminopyridineHCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 516892Sodium Bicarbonate

生成物 1

HCID 121090746-Aminopyridine-3-sulfonyl chloride収率 32.2%

反応条件

温度
150 °C

実験手順

Under ice-cooling, 10.00 g (0.106 mol) of 2-aminopyridine was added little by little to 123.8 g (1.06 mol) of chlorosulfonic acid. To the mixture was added 50.56 g (0.425 mol) of thionyl chloride. The mixture was heated under reflux for 2.5 hours, and further stirred at 150° C. for 7 hours. The reaction solution was poured into ice-water, neutralized by adding sodium bicarbonate and extracted with ethyl acetate. The organic layer was successively washed with an aqueous saturated sodium bicarbonate, water and brine, dried over magnesium sulfate, and then concentrated to dryness. The residue was suspended in ethyl ether and the insoluble matters were filtered off. The filtrate was concentrated to dryness and the residue was recrystallized from ethyl ether/hexane, to give 6.58 g of the title compound.

後処理

  1. temperatureUnder ice-cooling
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2.5 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was successively washed with an aqueous saturated sodium bicarbonate, water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness
  8. filtrationthe insoluble matters were filtered off
  9. concentrationThe filtrate was concentrated to dryness
  10. customthe residue was recrystallized from ethyl ether/hexane

出典と根拠

ORDレコード
ord-a81d5e998273470fac662f365f1097ed
出典データセット
uspto-grants-2010_11
特許番号
US07834049B2

反応ノート

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