Dimethylformamide → HCID 86729555、化合物

HRID 1426498ノート

反応式

HRID 1426498 の反応式
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

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 443297Hydroxyamine hydrochlorideHCID 13620271HCID 13620271、化合物

生成物 1

HCID 86729555HCID 86729555、化合物収率 43.4%

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6c53e5eed9904e4f8a3a61599235cefe
出典データセット
uspto-grants-2015_01
特許番号
US08933069B2

反応ノート

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