Toluene → HCID 67091069, compound

HRID 2353538Notes

Reaction equation

HRID 2353538 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=CC=C[C:3]=1[NH:8][NH2:9].[CH3:11][C:12]([CH3:19])([CH3:18])[C:13](=O)[CH2:14][C:15]#[N:16].[C:20]1(C)[CH:25]=CC=C[CH:21]=1>>[NH2:16][C:15]1[C:3]([N:8]2[CH:25]=[CH:20][CH:21]=[N:9]2)=[C:2]([CH3:10])[CH:7]=[C:13]([C:12]([CH3:19])([CH3:18])[CH3:11])[CH:14]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 67091069HCID 67091069, compoundYield 92%

Procedure

A solution of tolyl hydrazine hydrochloride (8.0 g, 50 mmol) and 4,4-dimethyl-3-oxo-pentanenitrile (6.3 g, 50 mmol) in toluene (30 mL) was heated to reflux overnight. Removal of the volatiles in vacuo provided a residue, which was purified by silica gel chromatography using 30% ethyl acetate in hexanes as the eluent. Concentration in vacuo provided 3-amino-5-tert-butyl-2-tolyl-2H-pyrazole as a brown solid (10.5 g, 92%). LC-MS analysis of the compound indicates the desired product is present with a purity >99%. Calculated mass=229. Observed mass=230.

Workup

  1. temperatureto reflux overnight
  2. customRemoval of the volatiles in vacuo
  3. customprovided a residue, which
  4. customwas purified by silica gel chromatography
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-3e64c7fd190f4e41907d6a4579a71a4e
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

Loading…