hydroxylamine-O-sulfonic acid → 4-Chlorothieno[3,2-c]pyridine-2-sulfonamide

HRID 569059

반응식

HRID 569059 반응식
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.C([N-:14]C(C)C)(C)C.[Li+].O.O.O.C([O-])(=O)C.[Na+].N[O:28][S:29]([OH:32])(=O)=O>O1CCCC1>[S:29]([C:9]1[S:10][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=2[CH:8]=1)(=[O:32])(=[O:28])[NH2:14]

참가 물질

6

반응물 4

HCID 76284hydroxylamine-O-sulfonic acidHCID 2724682Lithium diisopropylamideHCID 128273124-Chlorothieno[3,2-c]pyridineHCID 23665404Sodium Acetate Trihydrate

생성물 1

HCID 201485834-Chlorothieno[3,2-c]pyridine-2-sulfonamide수율 49%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 4-chlorothieno[3,2-c]pyridine (1.7 g, 10 mmol) in distilled tetrahydrofuran (25 ml), cooled to -70° C. and under a nitrogen atmosphere, was added dropwise 0.7 M lithium diisopropylamide in THF (16 ml, 11 mmol) to give a clear solution. After 178 hour, sulfur dioxide gas was bubbled over the reaction surface and it was gradually let warm to room temperature. The mixture was diluted with diethyl ether and the precipitated lithium sulfinate salt was collected by filtration. This salt (3.1 g) was dissolved in water (25 ml) and sodium acetate trihydrate (5.4 g, 66 mmol) and hydroxylamine-O-sulfonic acid (2.5 g, 22 mmol) were added. After stirring for 18 hours, the precipitated product was collected by filtration, dissolved in ethyl acetate, dried over anhydrous sodium sulfate, filtered through a pad of charcoal and the solvent was evaporated. The residue was recrystallized from ethyl acetate to give 1.23 g (49% yield) purified product.

후처리

  1. customto give a clear solution
  2. customsulfur dioxide gas was bubbled over the reaction surface and it
  3. additionThe mixture was diluted with diethyl ether
  4. filtrationthe precipitated lithium sulfinate salt was collected by filtration
  5. dissolutionThis salt (3.1 g) was dissolved in water (25 ml)
  6. filtrationthe precipitated product was collected by filtration
  7. dissolutiondissolved in ethyl acetate
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered through a pad of charcoal
  10. customthe solvent was evaporated
  11. customThe residue was recrystallized from ethyl acetate
  12. customto give 1.23 g (49% yield)
  13. custompurified product

출처 및 근거

ORD 기록
ord-acbd16478e7e48d1a213c0a4f5114cc9
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04731368

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