Triethylamine → 1-Tert-butyl-3-(4-chlorobenzyl)-1H-pyrazol-5-amine

HRID 1644638Notes

Reaction equation

HRID 1644638 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH2:10][C:11]#[N:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[C:22]([NH:26][NH2:27])([CH3:25])([CH3:24])[CH3:23]>C(O)C>[C:22]([N:26]1[C:11]([NH2:12])=[CH:10][C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:27]1)([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81889tert-Butylhydrazine monohydrochlorideHCID 509888474-(4-Chlorophenyl)-3-oxobutanenitrile

Product 1

HCID 575511731-Tert-butyl-3-(4-chlorobenzyl)-1H-pyrazol-5-amineYield 115.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(4-chloro-phenyl)-3-oxo-butyronitrile (500 mg, 2 mmol, 1.0 equiv), triethylamine (1.16 mL, 8.3 mmol, 3.2 equiv), and tert-butylhydrazine hydrochloride (1.03 g, 8.3 mmol, 3.2 equiv) in 10 mL of ethanol was heated at 100° C. in a sealed tube. After 4 d, the reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified via automated flash chromatography (40 g SiO2, gradient from hexanes to ethyl acetate) to afford the product as a yellow oil (610 mg, 70%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified

Sources & evidence

ORD record
ord-da5684ac0c8c47309f5c11f334e34c57
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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