Phosphorus oxychloride → HCID 90029196, compound

HRID 1488192Notes

Reaction equation

HRID 1488192 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:16]([NH2:18])=O)=[N:5][N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=1.O=P(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([C:16]#[N:18])=[N:5][N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:14])([CH3:13])[CH3:15])[CH:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 90029584HCID 90029584, compound2×

Product 1

HCID 90029196HCID 90029196, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole-3-carboxamide (compound 280.5, 1.08 g, 4.0 mmol) in toluene (25 mL) was added POCl3 (1.86 mL, 20.0 mmol) dropwise at 0° C. The mixture was stirred for 2 h at 50° C., then quenched with 30 mL of sodium bicarbonate (sat.). The aqueous phase was extracted with 2×100 mL of ethyl acetate and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:6) as the eluent to yield 500 mg (49%) of the title compound as a white solid.

Workup

  1. customquenched with 30 mL of sodium bicarbonate (sat.)
  2. extractionThe aqueous phase was extracted with 2×100 mL of ethyl acetate
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:6) as the eluent

Sources & evidence

ORD record
ord-e172201ca68e4146ab8b4ec50f3d699a
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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