Pentanenitrile, 4,4-dimethyl-3-oxo- → 3-tert-butyl-1-(4-tert-butylphenyl)-1H-pyrazol-5-amine

HRID 631735Notes

Reaction equation

HRID 631735 reaction equation
Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][NH2:13])=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[CH3:14][C:15]([CH3:22])([CH3:21])[C:16](=O)[CH2:17][C:18]#[N:19]>>[C:15]([C:16]1[CH:17]=[C:18]([NH2:19])[N:12]([C:9]2[CH:8]=[CH:7][C:6]([C:2]([CH3:5])([CH3:3])[CH3:4])=[CH:11][CH:10]=2)[N:13]=1)([CH3:22])([CH3:21])[CH3:14]

Participants

3

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 162174584-Tert-butylphenylhydrazine hydrochloride

Product 1

HCID 668764703-tert-butyl-1-(4-tert-butylphenyl)-1H-pyrazol-5-amineYield 73.7%

Procedure

Using the procedure in Example 161A Step 3, 4-tert-butylphenyl-hydrazine monohydrochloride (1.00 g, 4.98 mmol) and 4,4-dimethyl-3-oxopentanenitrile (625 mg, 4.98 mmol) were reacted to give 3-tert-butyl-1-(4-tert-butylphenyl)-1H-pyrazol-5-amine (996 mg, 3.67 mmol, 51%). 1H NMR (300 MHz, DMSO-d6) δ 7.46 (br s, 4H), 5.35 (s, 1H), 5.15 (br s, 2H), 1.30 (s, 9H), 1.20 (s, 9H); LC-MS (ESI) m/z 272 (M+H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-fb0d6eb8bfe248e9a2a5ac98d36650b9
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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