2-Methylbenzoyl chloride → 1-Methyl-5-(o-tolyl)-3-phenyl-1,2,4-triazole

HRID 1111868Notes

Reaction equation

HRID 1111868 reaction equation
Cl.[CH3:2][NH:3][NH:4][C:5](=[NH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:13]1([CH3:22])[C:14]([C:19](Cl)=O)=[CH:15][CH:16]=[CH:17][CH:18]=1>C(OCC)C>[CH3:2][N:3]1[C:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH3:22])=[N:12][C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N:4]1

Participants

4

Reactant 2

HCID 702762-Methylbenzoyl chlorideHCID 178486233HCID 178486233, compound

Product 1

HCID 218245451-Methyl-5-(o-tolyl)-3-phenyl-1,2,4-triazoleYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.56 g. of benzimidic acid 2-methylhydrazide hydrochloride and 3.8 g. of o-toluic acid chloride is heated under stirring at about 120° C. After cooling and addition of diethyl ether, the hydrochloride of the triazole is collected on filter and then suspended in a sodium bicarbonate aqueous solution. The free base is extracted with diethyl ether and the organic phase, after drying over sodium sulfate, is evaporated. The crude compound is purified by distillation at 160° C/0.1 mm Hg. Yield 76%.

Workup

  1. additionA mixture of 0.56 g
  2. temperatureAfter cooling
  3. customthe hydrochloride of the triazole is collected
  4. filtrationon filter
  5. extractionThe free base is extracted with diethyl ether
  6. dry with materialthe organic phase, after drying over sodium sulfate
  7. customis evaporated
  8. distillationThe crude compound is purified by distillation at 160° C/0.1 mm Hg

Sources & evidence

ORD record
ord-7fa73e849b2446649b87bcb0e40d9066
Source dataset
uspto-grants-1978_10
Patent number
US04119635

Reaction notes

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