HCID 178491626, compound → 5-(4-Methoxyphenyl)-3-methyl-1H-1,2,4-triazole

HRID 29813Notes

Reaction equation

HRID 29813 reaction equation
[NH:1]=[C:2]([NH:4][NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[CH3:3]>C(Cl)(Cl)Cl>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]2[N:1]=[C:2]([CH3:3])[NH:4][N:5]=2)=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 178491626HCID 178491626, compound

Product 1

HCID 5449015-(4-Methoxyphenyl)-3-methyl-1H-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

33.6 g (162 mmol) 4-methoxy-benzoic acid N′-(1-imino-ethyl)-hydrazide are heated to 180° C. for 30 minutes. After cooling the solidified melt is dissolved in 250 mL chloroform and repeatedly extracted with aqueous sodium hydroxide solution. The aqueous phases are combined, washed with chloroform, filtered and adjusted to an acid pH by the addition of glacial acetic acid. The precipitated solid is suction filtered, washed with water and dissolved by heating in chloroform. The solvent is evaporated down and the residue is filtered. The solid is washed with chloroform and diethyl ether.

Workup

  1. temperatureAfter cooling the solidified melt
  2. extractionrepeatedly extracted with aqueous sodium hydroxide solution
  3. washwashed with chloroform
  4. filtrationfiltered
  5. additionadjusted to an acid pH by the addition of glacial acetic acid
  6. filtrationfiltered
  7. washwashed with water
  8. dissolutiondissolved
  9. temperatureby heating in chloroform
  10. customThe solvent is evaporated down
  11. filtrationthe residue is filtered
  12. washThe solid is washed with chloroform and diethyl ether

Sources & evidence

ORD record
ord-decfad9cebdb4884915e86bec2bb65a5
Source dataset
uspto-grants-2008_09
Patent number
US07423036B2

Reaction notes

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