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

HRID 1173091노트

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HRID 1173091 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

HCID 121090746-Aminopyridine-3-sulfonyl chloride수율 32.2%

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온도
150 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a81d5e998273470fac662f365f1097ed
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834049B2

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