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Pyridine → 2,4-Dinitrobenzenesulfonamide

HRID 6904
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HRID 6904 반응식
C(O)(C(F)(F)F)=O.[N:8]1C=CC=CC=1.[N+:14]([C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[S:26](Cl)(=[O:28])=[O:27])([O-:16])=[O:15].S(Cl)(Cl)(=O)=O>C(Cl)Cl.C1COCC1>[N+:14]([C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[S:26]([NH2:8])(=[O:28])=[O:27])([O-:16])=[O:15]
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참가 물질

7

반응물 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 24648Sulfuryl chlorideHCID 74255Benzenesulfonyl chloride, 2,4-dinitro-

생성물 1

HCID 109118542,4-Dinitrobenzenesulfonamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

A solution of Part A compound (1.01 g, 2.37 mmol) and TFA (8 mL) in CH2Cl2 (30 mL) was stirred at RT for 4.5 h. The solution was concentrated in vacuo, and the residue was dissolved in CH2Cl2 and filtered through a pad of solid K2CO3. The filtrate was concentrated in vacuo to give the corresponding crude amine. To a solution of the crude amine in THF (11.9 mL) were added pyridine (0.383 mL, 4.74 mmol) and 2,4-dinitrobenzenesulfonyl chloride (0.85 g, 3.19 mmol) and the solution was stirred at RT for 15 h. Since some starting material still remained at this point, more sulfonyl chloride (0.32 g, 1.2 mmol) was then added. After a further 4 h, HPLC analysis indicated that all starting material had been consumed. The reaction mixture was diluted with Et2O, washed with 1N aq HCl, saturated aq NaHCO3 and brine, dried (MgSO4), filtered and concentrated in vacuo to provide the crude 2,4-dinitrobenzenesulfonamide

후처리

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. filtrationfiltered through a pad of solid K2CO3
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give the corresponding crude amine
  6. additionwas then added
  7. waitAfter a further 4 h
  8. customhad been consumed
  9. additionThe reaction mixture was diluted with Et2O
  10. washwashed with 1N aq HCl, saturated aq NaHCO3 and brine
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3378496704a04e2a9685d0d6d1f3e5fe
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07084162B2

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