Dimethylformamide → HCID 86729555, 화합물

HRID 1426498노트

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HRID 1426498 반응식
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:13]1[C:17]([CH3:18])=[C:16]([C:19](=O)[CH3:20])[CH:15]=[N:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[ClH:22].NO.[OH-].[Na+].C[N:28]([CH3:31])C=O>>[CH2:6]([N:13]1[C:17]([CH3:18])=[C:16](/[C:19](/[Cl:22])=[CH:20]/[C:31]#[N:28])[CH:15]=[N:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

6

반응물 5

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 443297Hydroxyamine hydrochlorideHCID 13620271HCID 13620271, 화합물

생성물 1

HCID 86729555HCID 86729555, 화합물수율 43.4%

실험 절차

To N,N-dimethylformamide (17.55 g) was added phosphorus oxychloride (36.8 g) by small portions under ice-cooling, the mixture was stirred at room temperature for 15 min. Thereto was added 1-(1-benzyl-5-methyl-1H-pyrazol-4-yl)ethanone (12.86 g) produced above by small portions under ice-cooling, and the reaction mixture was stirred at 50° C. for 30 min. Thereto was added a powder (33.40 g) of hydroxylamine hydrochloride at 50° C. by small portions, and the reaction mixture was stirred at 50° C. for 30 min. Ice water (200 mL) was added to the reaction mixture, and the mixture was neutralized with 1M aqueous sodium hydroxide solution, and extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with brine (20 mL) and dried over anhydrous magnesium sulfate. Insoluble material was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane), and crystallized from diethylether to give the title compound (6.71 g) as a pale-yellow powder.

후처리

  1. temperaturecooling
  2. customproduced above by small portions under ice-
  3. temperaturecooling
  4. stirringthe reaction mixture was stirred at 50° C. for 30 min
  5. stirringthe reaction mixture was stirred at 50° C. for 30 min
  6. extractionextracted with ethyl acetate (100 mL×2)
  7. washThe combined organic layers were washed with brine (20 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customInsoluble material was removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  12. customcrystallized from diethylether

출처 및 근거

ORD 기록
ord-6c53e5eed9904e4f8a3a61599235cefe
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933069B2

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