Iodoethane → HCID 14590584, compound

HRID 494364Notes

Reaction equation

HRID 494364 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH2:11])=[N:8][NH:9][CH:10]=1)=[O:5])[CH3:2].[H-].[Na+].[CH2:14](I)[CH3:15].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(#N)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH2:11])=[N:8][N:9]([CH2:14][CH3:15])[CH:10]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24436Sodium SulfateHCID 24758Sodium hydrideHCID 178469928HCID 178469928, compound

Product 1

HCID 14590584HCID 14590584, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-amino-1H-pyrazole-4-carboxylic acid ethyl ester (5.0 g, 32 mmol) in acetonitrile is added sodium hydride (1.28 g, 32 mmol) at RT. After 30 min of stirring, a solution of ethyl iodide (2.57 ml, 32 mmol) in acetonitriloe is added dropwise. The reaction mixture is stirred at RT for 16 h. Water is added followed by anhydrous sodium sulfate. The mixture is filtered and concentrated at reduced pressure. The crude product is chromatographed on silica gel using 30% ethyl acetate in hexanes to provide a regioisomeric mixture of N-ethylated 3-amino-1H-pyrazole-4-carboxylic acid ethyl esters. This mixture is used in the following reaction step without further purification.

Workup

  1. stirringThe reaction mixture is stirred at RT for 16 h
  2. filtrationThe mixture is filtered
  3. concentrationconcentrated at reduced pressure
  4. customThe crude product is chromatographed on silica gel using 30% ethyl acetate in hexanes
  5. customto provide
  6. customThis mixture is used in the following reaction step without further purification

Sources & evidence

ORD record
ord-0be3875414ae4139b110bbd813c61961
Source dataset
uspto-grants-2009_05
Patent number
US07538135B2

Reaction notes

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