N-methylbenzohydrazide → 1-Methyl-3-(o-tolyl)-5-phenyl-1,2,4-triazole

HRID 26649Notes

Reaction equation

HRID 26649 reaction equation
C(O[C:4]([C:6]1[C:7]([CH3:12])=[CH:8][CH:9]=[CH:10][CH:11]=1)=[NH:5])C.[CH3:13][N:14]([C:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH2:15]>C(OCC)C>[CH3:13][N:14]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:5][C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH3:12])=[N:15]1

Participants

4

Reactant 2

HCID 242395N-methylbenzohydrazideHCID 12690380Benzenecarboximidic acid, 2-methyl-, ethyl ester

Product 1

HCID 213219391-Methyl-3-(o-tolyl)-5-phenyl-1,2,4-triazoleYield 32%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.14 g. of o-toluimidic acid ethyl ester, 1.14 g. of 1-methyl-1-benzoylhydrazine and 0.1 g. of o-toluimidic acid ester hydrochloride, as a catalyst, is heated at about 100° C. for three hours under reduced pressure (about 200 mm Hg) and then at about 120° C. for five hours. The raw material is taken up with diethyl ether and the organic solution is washed with aqueous sodium bicarbonate and then dried over Na2SO4. After evaporation of the solvent, the product is distilled at 170° C./0.1 mm Hg. Yield 32%.

Workup

  1. additionA mixture of 1.14 g
  2. washthe organic solution is washed with aqueous sodium bicarbonate
  3. dry with materialdried over Na2SO4
  4. customAfter evaporation of the solvent
  5. distillationthe product is distilled at 170° C./0.1 mm Hg

Sources & evidence

ORD record
ord-5e6fa32054c148dd8ee0259a0174523f
Source dataset
uspto-grants-1979_04
Patent number
US04151169

Reaction notes

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