Hydrochloric Acid → 1-Methyl-3-(3-chlorophenyl)-5-(o-tolyl)-1,2,4-triazole

HRID 26650Notes

Reaction equation

HRID 26650 reaction equation
[CH3:1][N:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1C)[NH2:3].C(O[C:14](=[NH:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1)C.Cl.[Na].[CH2:25](O)[CH3:26]>>[CH3:1][N:2]1[C:4]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:25]=2[CH3:26])=[N:22][C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[N:3]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5360545SodiumHCID 11126933Ethyl 3-chlorobenzene-1-carboximidate2×HCID 137613951-Methyl-1-(2-methylphenyl)hydrazine

Product 1

HCID 213219361-Methyl-3-(3-chlorophenyl)-5-(o-tolyl)-1,2,4-triazoleYield 66%

Conditions

Temperature
65 °C

Procedure

A mixture of 6.85 g. of 1-methyl-1-(o-toluyl)-hydrazine, 13.8 g. of m-chlorobenzimidic acid ethyl ester and 1.8 g. of the hydrochloride of m-chlorobenzimidic acid ethyl ester is heated with stirring under vacuum for 18 hours and simultaneously ethanol and m-chlorobenzonitrile are distilled off. Then, maintaining the temperature at about 65° C., 40 ml. of ethanol are added followed by a sodium ethylate solution prepared from 0.336 g. of sodium and 20 ml. of ethanol. The mixture is refluxed for 6 hours and after standing over night, the insoluble precipitate is filtered off. The filtrate is evaporated to dryness. The residue is dissolved in 100 ml. of diethyl ether and after washing the organic layer successively with aqueous 5% Na2CO3, 5% HCl and water, the solution is dried over sodium sulfate. The crude product obtained by evaporation of the diethyl ether solution is crystallized from ethanol. Yield 66%. M.p. 77°-78° C.

Workup

  1. additionA mixture of 6.85 g
  2. distillationsimultaneously ethanol and m-chlorobenzonitrile are distilled off
  3. additionof ethanol are added
  4. customprepared from 0.336 g
  5. temperatureThe mixture is refluxed for 6 hours
  6. waitafter standing over night
  7. filtrationthe insoluble precipitate is filtered off
  8. customThe filtrate is evaporated to dryness
  9. dissolutionThe residue is dissolved in 100 ml
  10. washof diethyl ether and after washing the organic layer successively with aqueous 5% Na2CO3, 5% HCl and water
  11. dry with materialthe solution is dried over sodium sulfate

Sources & evidence

ORD record
ord-5e17c00ba76240e2aaf65ec90239c013
Source dataset
uspto-grants-1979_04
Patent number
US04151169

Reaction notes

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