Dimethylformamide → HCID 21628283, compound

HRID 1488209Notes

Reaction equation

HRID 1488209 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][C:10]([CH3:13])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl.[OH-].[Na+].CN(C)[CH:23]=[O:24]>O>[CH2:1]([N:8]1[CH:12]=[C:11]([CH:23]=[O:24])[C:10]([CH3:13])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 10419637HCID 10419637, compound2×

Product 1

HCID 21628283HCID 21628283, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-benzyl-3-methyl-1H-pyrazole (compound 314.1, 1.00 g, 5.81 mmol) in N,N-dimethylformamide (3 mL) was added POCl3 (493 μL, 5.28 mmol) dropwise. The reaction mixture was stirred for 3 h at 90° C. under nitrogen. The reaction mixture was diluted with 50 mL of H2O. The pH of the solution was adjusted to 7 with sodium hydroxide (2 M). The aqueous phase was extracted with 3×20 mL of ethyl acetate and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 1.42 g (crude) of the title compound as a brown oil.

Workup

  1. extractionThe aqueous phase was extracted with 3×20 mL of ethyl acetate
  2. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e9d61c969c3418483cc579bff194006
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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