Triethylamine → 5-Amino-1-cyclohexyl-1H-pyrazole-4-carbonitrile

HRID 1664481

Reaction equation

HRID 1664481 reaction equation
C(O[CH:4]=[C:5]([C:8]#[N:9])[C:6]#[N:7])C.C(N(CC)CC)C.Cl.[CH:18]1([NH:24][NH2:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C>[NH2:9][C:8]1[N:24]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[N:25]=[CH:4][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 671522-(Ethoxymethylene)propanedinitrileHCID 207836Cyclohexylhydrazine hydrochloride

Product 1

HCID 6900055-Amino-1-cyclohexyl-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First ethoxymethylenemalononitrile (2.43 g, 19.9 mmol) and then 8 ml of triethylamine are added to a solution of cyclohexylhydrazine hydrochloride (3 g, 19.9 mmol) in 36 ml of ethanol at room temperature. The mixture is refluxed for 20 min and then cooled. The solvent is stripped off in a rotary evaporator, and the residue is taken up in DCM, washed with aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product is chromatographed on silica gel (mobile phase: dichloromethane/methanol 0-10%).

Workup

  1. temperatureThe mixture is refluxed for 20 min
  2. temperaturecooled
  3. customThe solvent is stripped off in a rotary evaporator
  4. washwashed with aqueous sodium bicarbonate solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is chromatographed on silica gel (mobile phase: dichloromethane/methanol 0-10%)

Sources & evidence

ORD record
ord-677fc99bffc945709f49fc9b470fb088
Source dataset
uspto-grants-2011_10
Patent number
US08039477B2

Linked notes

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