Dimethylformamide → HCID 86729550, compound

HRID 1426458Notes

Reaction equation

HRID 1426458 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:13]1[CH:17]=[C:16]([C:18](=O)[CH3:19])[C:15]([CH3:21])=[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[CH:17]=[C:16](/[C:18](/[Cl:22])=[CH:19]/[C:31]#[N:28])[C:15]([CH3:21])=[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 6493177HCID 6493177, compound

Product 1

HCID 86729550HCID 86729550, compound

Procedure

To N,N-dimethylformamide (13.4 g) was added phosphorus oxychloride (28.1 g) by small portions under ice-cooling, and the mixture was stirred at room temperature for 15 min. Thereto was added 1-(1-benzyl-3-methyl-1H-pyrazol-4-yl)ethanone (9.80 g) produced above by small portions under ice-cooling, and the reaction mixture was stirred at 50° C. for 30 min. Thereto was added hydroxylamine hydrochloride in a powder (25.4 g) 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 diethyl ether to give the title compound (5.73 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 diethyl ether

Sources & evidence

ORD record
ord-9f820c17e0194025b55d7ee029b9766a
Source dataset
uspto-grants-2015_01
Patent number
US08933069B2

Reaction notes

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