Water → HCID 178438403, compound

HRID 2260041Notes

Reaction equation

HRID 2260041 reaction equation
[CH2:1]([C:4]1[NH:8][N:7]=[C:6]([NH:9][C:10](=[N:12]O)[CH3:11])[CH:5]=1)[CH2:2][CH3:3].N1C=CC=CC=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>CN(C)C(=O)C>[CH3:11][C:10]1[NH:9][C:6]2[N:7]([N:8]=[C:4]([CH2:1][CH2:2][CH3:3])[CH:5]=2)[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 178439388HCID 178439388, compound

Product 1

HCID 178438403HCID 178438403, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A 5.38 g portion of N-(5-propyl-1H-pyrazol-3-yl)acetamidoxime was dissolved in 45 ml of N,N-dimethylacetamide. With cooling on an ice bath, to this were added 2.39 ml of pyridine and 5.63 g of p-toluenesulfonic acid chloride, followed by 30 minutes of stirring at the same temperature and additional 3 hours of stirring at room temperature. The resulting reaction mixture was added to 350 ml of water and extracted with chloroform. After distilling off chloroform from the organic layer under a reduced pressure, the thus obtained residue was dissolved in 135 ml of methanol, mixed with 2.39 ml of pyridine and then heated under reflux for 2 hours.

Workup

  1. temperatureWith cooling on an ice bath
  2. stirringof stirring at room temperature
  3. customThe resulting reaction mixture
  4. extractionextracted with chloroform
  5. distillationAfter distilling off chloroform from the organic layer under a reduced pressure
  6. dissolutionthe thus obtained residue was dissolved in 135 ml of methanol
  7. additionmixed with 2.39 ml of pyridine
  8. temperatureheated
  9. temperatureunder reflux for 2 hours

Sources & evidence

ORD record
ord-6e1ac42171a44cb1baf37efc7ed56d9a
Source dataset
uspto-grants-1995_12
Patent number
US05475114

Reaction notes

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