Pentanenitrile, 4,4-dimethyl-3-oxo- → HCID 66876820, compound

HRID 631683Notes

Reaction equation

HRID 631683 reaction equation
[ClH:1].[CH:2]1([NH:8][NH2:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:10][C:11]([CH3:18])([CH3:17])[C:12](=O)[CH2:13][C:14]#[N:15]>C(O)C>[ClH:1].[C:11]([C:12]1[CH:13]=[C:14]([NH2:15])[N:8]([CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[N:9]=1)([CH3:18])([CH3:17])[CH3:10]

Participants

4

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 207836Cyclohexylhydrazine hydrochloride

Product 1

HCID 66876820HCID 66876820, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of cyclohexylhydrazine hydrochloride (1.5 g, 9.96 mmol) and 4,4-dimethyl-3-oxopentanenitrile (1.5 g, 11.98 mmol) in ethanol (5 mL) was refluxed for 15 h. After cooling to rt, the reaction mixture was concentrated under reduced pressure and the obtained crude product was recrystallized from a mixture of diethyl ether and petroleum ether to afford 3-tert-butyl-1-cyclohexyl-1H-pyrazol-5-amine hydrochloride (1.0 g, 39%) as colorless solid. 1H NMR (400 MHz, DMSO-d6) δ13.24 (brs, 1H), 7.02 (brs, 2H), 5.52 (s, 1H), 4.30 (m, 1H), 1.63-1.98 (m, 7H), 1.10-1.40 (m, 12H); LC-MS (ESI) m/z 222 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe obtained crude product
  3. customwas recrystallized from a mixture of diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-a8cc1249a57e4c6c8d18a771efc068c0
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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