Phenylhydrazine → 5,6-Dichloro-3-[(2-phenylhydrazono)methyl]pyrazinamine

HRID 1633225Notes

Reaction equation

HRID 1633225 reaction equation
[NH2:1][C:2]1[C:3]([CH:10]=O)=[N:4][C:5]([Cl:9])=[C:6]([Cl:8])[N:7]=1.[C:12]1([NH:18][NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[Cl:9][C:5]1[N:4]=[C:3]([CH:10]=[N:19][NH:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]([NH2:1])=[N:7][C:6]=1[Cl:8]

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 133678713-Amino-5,6-dichloropyrazine-2-carbaldehyde

Product 1

HCID 861142925,6-Dichloro-3-[(2-phenylhydrazono)methyl]pyrazinamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.96 gram (0.005 mole) of 3-amino-5,6-dichloropyrazinaldehyde, 0.54 gram (0.005 mole) of phenylhydrazine and 20 milliliters of ethanol were heated with stirring and refluxed for 10 minutes to obtain a 5,6-dichloro-3-[(2-phenylhydrazono)methyl]pyrazinamine product as a solid. The reaction mixture was allowed to cool and the solid product recovered by filtration and recrystallized from ethanol to obtain 0.71 gram (50 percent yield) of purified product as yellow flakes, m.p. 277°-278° C. (dec.). Elemental analyses were as follows:

Workup

  1. temperaturerefluxed for 10 minutes

Sources & evidence

ORD record
ord-f2386d1782f74632ad5d3ef67d28e7fb
Source dataset
uspto-grants-1984_10
Patent number
US04479953

Reaction notes

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