Iodoethane → (3-amino-1-ethyl-1H-pyrazol-4-yl)-phenyl-methanone

HRID 494369Notes

Reaction equation

HRID 494369 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:5][NH:4][N:3]=1.[H-].[Na+].[CH2:17](I)[CH3:18]>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[C:6]([C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:8])=[CH:5][N:4]([CH2:17][CH3:18])[N:3]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178509267HCID 178509267, compound

Product 1

HCID 68866724(3-amino-1-ethyl-1H-pyrazol-4-yl)-phenyl-methanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a vigorously stirring solution of (3-amino-1H-pyrazol-4-yl)-phenyl-methanone (0.1 g, 0.53 mmol) in dry DMF at RT is added sodium hydride (0.023 g, 0.57 mmol). After 1 h, ethyl iodide (0.042 mL, 0.53 mmol) is added and stirring is continued for 4 h. The reaction mixture is diluted with ethyl acetate, washed with water, brine and dried over anhydrous sodium sulfate. The organic filtrate is concentrated and the crude is chromatographed on silica gel using 50% ethyl acetate in hexanes to provide (3-amino-1-ethyl-1H-pyrazol-4-yl)-phenyl-methanone.

Workup

  1. waitis continued for 4 h
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe organic filtrate is concentrated
  5. customthe crude is chromatographed on silica gel using 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8126096e5b3b44298db9109978e0fb0d
Source dataset
uspto-grants-2009_05
Patent number
US07538135B2

Reaction notes

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