Methanesulfonic Acid → HCID 178433898, compound

HRID 497951Notes

Reaction equation

HRID 497951 reaction equation
CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:20]([C:28](=[CH:34][NH:35][C:36]1[N:40]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[N:39]=[C:38]([CH3:47])[CH:37]=1)[C:29]([O:31]CC)=O)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>O>[OH:31][C:29]1[C:28]([C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:27])=[CH:34][N:35]=[C:36]2[N:40]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=3)[N:39]=[C:38]([CH3:47])[C:37]=12

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 178471942HCID 178471942, compound

Product 1

HCID 178433898HCID 178433898, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methanesulfonic acid (30 mL) and phosphorus pentoxide (6 g) was heated at 100° C. The mixture was stirred thoroughly at the temperature, with gradual addition of powdery ethyl 2-benzoyl-3-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]-2-propenoate (3.0 g, 8.0 mmol). The mixture was further heated and stirred at the temperature for 30 minutes. The solution was cooled to room temperature, iced water was added thereto. The solution was neutralized by the addition of an aqueous sodium hydroxide solution, and organic matter was extracted with chloroform. The extract was washed with saturated brine and water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Purification of the residue by basic silica gel column chromatography (chloroform) gave the title compound (880 mg, 34% yield).

Workup

  1. temperatureThe mixture was further heated
  2. temperatureThe solution was cooled to room temperature
  3. extractionwas extracted with chloroform
  4. washThe extract was washed with saturated brine and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customPurification of the residue by basic silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-25521c3303a343458a0fca3d13bc5e41
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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