Pyridine → HCID 178469934, compound

HRID 429667Notes

Reaction equation

HRID 429667 reaction equation
[OH:1][N:2]=[C:3]([NH:5][C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][NH:8][N:7]=1)[CH3:4].N1C=CC=CC=1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>CN(C)C=O.C(OCC)(=O)C.O>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([O:1][N:2]=[C:3]([NH:5][C:6]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][NH:8][N:7]=2)[CH3:4])(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 178469933HCID 178469933, compound

Product 1

HCID 178469934HCID 178469934, compoundYield 82.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 3-[[1-(hydroxyimino)ethyl]amino]-pyrazole-4-carboxylate (1.50 g) and pyridine (1.12 g) in N,N-dimethylformamide (20 ml) was added dropwise p-toluenesulfonyl chloride (1.39 g) under ice bath cooling and stirred at ambient temperature for 3 hours. The reaction mixture was diluted with ethyl acetate and water. The organic layer was separated and washed with saturated sodium hydrogen carbonate aqueous solution and brine. The solution was dried over magnesium sulfate and concentrated in vacuo to give ethyl 3-[1-(p-toluenesulfonyloxyimino)ethyl]amino-1H-pyrazole-4-carboxylate (2.14 g).

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. washwashed with saturated sodium hydrogen carbonate aqueous solution and brine
  4. dry with materialThe solution was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c462cc486c384f249aa9ff9909fcbc73
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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