Acrylonitrile → 1H-Pyrazol-3-amine, 1-(4-bromophenyl)-

HRID 877025Notes

Reaction equation

HRID 877025 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[C:10](#[N:13])[CH:11]=[CH2:12].[O-]CC.[Na+].BrN1C(=O)CCC1=O>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([NH2:13])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 121584-BromophenylhydrazineHCID 67184N-bromobutanimideHCID 2723922Sodium ethoxide

Product 1

HCID 234642851H-Pyrazol-3-amine, 1-(4-bromophenyl)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared by the reaction of 4-bromophenylhydrazine with acrylonitrile in the presence of a suitable base such as sodium ethoxide in refluxing ethanol followed by oxidation with N-bromosuccinimide; 1H NMR (300 MHz, DMSO-d6) δ 3.81 (br s, 2H), 5.84 (s, 1H), 7.41 (d, J=8.7 Hz, 2H), 7.47 (d, J=8.7 Hz, 2H), 7.63 (s, 1H).

Sources & evidence

ORD record
ord-ddd107b0316c4273a22a7449da03b613
Source dataset
uspto-grants-2015_03
Patent number
US08987278B2

Reaction notes

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