Bromine → 5-(3-benzenesulfonylpropyl)4-bromo-1-butyl-1H-pyrazole-3-carbonitrile

HRID 1984473

반응식

HRID 1984473 반응식
C([O-])(=O)C.[K+].[C:6]1([S:12]([CH2:15][CH2:16][CH2:17][C:18]2[N:22]([CH2:23][CH2:24][CH2:25][CH3:26])[N:21]=[C:20]([C:27]#[N:28])[CH:19]=2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br:29]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C>[C:6]1([S:12]([CH2:15][CH2:16][CH2:17][C:18]2[N:22]([CH2:23][CH2:24][CH2:25][CH3:26])[N:21]=[C:20]([C:27]#[N:28])[C:19]=2[Br:29])(=[O:13])=[O:14])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

참가 물질

6

반응물 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 517044Potassium AcetateHCID 669583215-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carbonitrile

생성물 1

HCID 669585995-(3-benzenesulfonylpropyl)4-bromo-1-butyl-1H-pyrazole-3-carbonitrile수율 45.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Potassium acetate (3.82 g, 38.9 mmol) was added to a solution of 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carbonitrile (8.60 g, 25.9 mmol) in 50 mL of acetic acid. The reaction mixture was stirred until all solids had dissolved, followed by dropwise addition of bromine (1.33 mL, 25.9 mmol) over 5 minutes. The resultant red solution was stirred for 5 hours and aqueous sodium thiosulfate was added to quench excess bromine. The reaction mixture was concentrated under reduced pressure and the residue was diluted with 200 mL of water. The pH of the mixture was adjusted to 8-9 by slow addition of solid sodium carbonate followed by extraction with several portions of ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford an orange oil. Purification via flash column chromatography on silica gel (eluting with hexane:ethyl acetate in a gradient from 3:1 to 1:1) afforded 4.80 g of 5-(3-benzenesulfonylpropyl)-4-bromo-1-butyl-1H-pyrazole-3-carbonitrile as a colorless oil that crystallized upon standing.

후처리

  1. dissolutionhad dissolved
  2. stirringThe resultant red solution was stirred for 5 hours
  3. customto quench excess bromine
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionthe residue was diluted with 200 mL of water
  6. additionThe pH of the mixture was adjusted to 8-9 by slow addition of solid sodium carbonate
  7. extractionfollowed by extraction with several portions of ethyl acetate
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto afford an orange oil
  13. customPurification via flash column chromatography on silica gel (
  14. washeluting with hexane

출처 및 근거

ORD 기록
ord-8d224dfa6603409f8a57f8d832e80a00
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544697B2

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