Water → 1-Methyl-1H-pyrazole-4-sulfonic acid methyl-(2-oxo-ethyl)-amide

HRID 553500Notes

Reaction equation

HRID 553500 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]([CH3:15])[S:6]([C:9]1[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=1)(=[O:8])=[O:7].O.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH3:15][N:5]([CH2:4][CH:3]=[O:2])[S:6]([C:9]1[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=1)(=[O:7])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 673674041-Methyl-1H-pyrazole-4-sulfonic acid (2,2-dimethoxy-ethyl)-methyl-amide

Product 1

HCID 866402111-Methyl-1H-pyrazole-4-sulfonic acid methyl-(2-oxo-ethyl)-amideYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Alternatively, 1-methyl-1H-pyrazole-4-sulfonic acid (2,2-dimethoxy-ethyl)-methyl-amide (1.0 equivalents) is suspended in toluene (5 volumes) and water (0.5 volumes) and trifluoroacetic acid is added keeping the temperature below 25° C. The resulting solution is allowed to stir for at least 8 hours below 25° C. and sampled for reaction completion. Once the reaction is deemed complete the solution is concentrated to an oil. The resulting oil is dissolved in brine (7.5 volumes) and water (2.5 volumes). Potassium carbonate is added portion wise to keep the temperature below 25° C. until a pH of 7.5 is achieved. The reaction is then washed with methylene chloride (3×10 volumes) and the combined organic layers are dried with sodium sulfate (200 wt %). The slurry is then filtered and the cake washed with methylene chloride (2×3 volumes). The resulting filtrate is held under vacuum for ≧24 hr., to concentrate the title preparation to a viscous amber oil (92% yield).

Workup

  1. customthe temperature below 25° C
  2. aliquotsampled for reaction completion
  3. concentrationis concentrated to an oil
  4. dissolutionThe resulting oil is dissolved in brine (7.5 volumes)
  5. additionPotassium carbonate is added portion wise
  6. customthe temperature below 25° C.
  7. washThe reaction is then washed with methylene chloride (3×10 volumes)
  8. dry with materialthe combined organic layers are dried with sodium sulfate (200 wt %)
  9. filtrationThe slurry is then filtered
  10. washthe cake washed with methylene chloride (2×3 volumes)
  11. waitThe resulting filtrate is held under vacuum for ≧24 hr
  12. concentration, to concentrate the title

Sources & evidence

ORD record
ord-f31ccd9ab98f4af99c386479f5aaad00
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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