Sodium Bicarbonate → HCID 178466780, compound

HRID 1773786Notes

Reaction equation

HRID 1773786 reaction equation
CN(C)S([N:6]1[C:10]([C:11](=[O:13])[CH3:12])=[CH:9][C:8]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:7]1)(=O)=O.C([O-])(O)=O.[Na+]>Cl.CO>[O:15]([CH2:14][C:8]1[CH:9]=[C:10]([C:11](=[O:13])[CH3:12])[NH:6][N:7]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 679600925-Acetyl-3-phenoxymethyl-pyrazole-1-sulfonic acid dimethylamide

Product 1

HCID 178466780HCID 178466780, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

5-Acetyl-3-phenoxymethyl-pyrazole-1-sulfonic acid dimethylamide (0.1 g, 0.32 mmol) was dissolved in a 1.25M solution of HCl in methanol (3.79 mL) in a sealed tube and under nitrogen. The mixture was stirred at 65° C. for 24 hours, then basified with a saturated solution of NaHCO3 and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 40/60). The desired fractions were collected and the solvents evaporated in vacuo to yield 1-(5-phenoxymethyl-2H-pyrazol-3-yl)-ethanone (55 mg, 81% yield) as a white solid.

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 40/60)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-ea779ff78cb64d4383ddca44e78dda7c
Source dataset
uspto-grants-2016_02
Patent number
US09255103B2

Reaction notes

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