P-Anisidine → 5,6-Dichloro-3-[(4-methoxyphenyl)imino]methylpyrazinamine

HRID 1633236Notes

Reaction equation

HRID 1633236 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.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1>C(O)C>[Cl:9][C:5]1[N:4]=[C:3]([CH:10]=[N:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[C:2]([NH2:1])=[N:7][C:6]=1[Cl:8]

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 133678713-Amino-5,6-dichloropyrazine-2-carbaldehyde

Product 1

HCID 133678765,6-Dichloro-3-[(4-methoxyphenyl)imino]methylpyrazinamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a manner similar to that described in Example 9, 1.92 grams (0.01 mole) of 3-amino-5,6-dichloropyrazinaldehyde, 1.23 g (0.01 mole) of p-anisidine and 15 milliliters of ethanol were mixed together and heated at reflux temperature to obtain a 5,6-dichloro-3-[(4-methoxyphenyl)imino]methylpyrazinamine product which precipitated in the reaction mixture. The product was recovered by filtration, recrystallized from ethanol to obtain 2.14 grams of a purified product, m.p. 167°-168° C. (dec). Elemental analyses were as follows:

Workup

  1. additionwere mixed together
  2. temperatureheated
  3. temperatureat reflux temperature

Sources & evidence

ORD record
ord-e180cb2eaed342a69208ad1b5b66f797
Source dataset
uspto-grants-1984_10
Patent number
US04479953

Reaction notes

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