Triethylamine → 5-Amino-1-(2-ethylphenyl)-1H-pyrazole-4-carbonitrile

HRID 1434536

Reaction equation

HRID 1434536 reaction equation
Cl.[CH2:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][NH2:11])[CH3:3].C(O[CH:15]=[C:16]([C:19]#[N:20])[C:17]#[N:18])C.C(N(CC)CC)C>C(O)C.ClCCl>[NH2:20][C:19]1[N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:2][CH3:3])[N:11]=[CH:15][C:16]=1[C:17]#[N:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 671522-(Ethoxymethylene)propanedinitrileHCID 27332092-Ethylphenylhydrazine Hydrochloride

Product 1

HCID 121505585-Amino-1-(2-ethylphenyl)-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3.0 g (17.0 mmol) of 2-ethylphenylhydrazine hydrochloride and 2.12 g (17.0 mmol) of ethoxymethylenemalononitrile in 36 ml of ethanol is mixed with 7.1 ml (51.1 mmol) of triethylamine and heated at 60° C. until the reaction is complete according to a TLC check (about 30 min). For working up, the solvent is stripped off, and the residue is taken up in dichloromethane, washed with saturated sodium bicarbonate solution and dried over sodium sulphate. Concentration results in a crude product which is purified by column chromatography on silica gel (mobile phase dichloromethane with 0-10% methanol). 3.05 g (83.5% of theory) of the desired product are obtained.

Workup

  1. customis complete according to a TLC check (about 30 min)
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried over sodium sulphate
  4. concentrationConcentration
  5. customresults in a crude product which
  6. customis purified by column chromatography on silica gel (mobile phase dichloromethane with 0-10% methanol)

Sources & evidence

ORD record
ord-5b5cc3eef82b4f35b12de8a0f0d7a9a4
Source dataset
uspto-grants-2009_11
Patent number
US07615558B2

Linked notes

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