Dimethylformamide → HCID 17863259, compound

HRID 1592820Notes

Reaction equation

HRID 1592820 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([CH3:14])[N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN(C)[CH:30]=[O:31]>>[CH2:1]([O:8][C:9]1[C:13]([CH:30]=[O:31])=[C:12]([CH3:14])[N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 17863262HCID 17863262, compound

Product 1

HCID 17863259HCID 17863259, compound

Procedure

To a solution of 3-benzyloxy-5-methyl-1-phenyl-1H-pyrazole (5.1 g) in N,N-dimethylformamide (30 mL) was added phosphorus oxychloride (2.2 mL) at 80° C., and the mixture was stirred for 1 hour. After cooling to room temperature, the reaction mixture was poured into 1 mol/L aqueous sodium hydroxide solution. The mixture was extracted with diethyl ether, and the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane) to give the title compound (4.6 g).

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane)

Sources & evidence

ORD record
ord-66ac1ecf6fe04f2388f421ce142909d4
Source dataset
uspto-grants-2007_11
Patent number
US07294618B2

Reaction notes

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