Dimethylformamide → HCID 86729555, compound

HRID 1409094Notes

Reaction equation

HRID 1409094 reaction equation
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

Participants

6

Reactant 5

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

Product 1

HCID 86729555HCID 86729555, compoundYield 43.4%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-650e73f9c3094162a462e20dab942883
Source dataset
uspto-grants-2014_12
Patent number
US08921354B2

Reaction notes

Loading…