Triethylamine → 3-ethyl-4-(4-methoxyphenyl)-5-(4-nitro-3-methylphenyl)-4H-1,2,4-triazole

HRID 1197869

Reaction equation

HRID 1197869 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17](Cl)[C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([CH3:27])[CH:19]=2)=[CH:12][CH:11]=1.[C:29]([NH:33][NH2:34])(=O)[CH2:30][CH3:31]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.O>[CH2:30]([C:29]1[N:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[CH:11][CH:12]=2)[C:17]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([CH3:27])[CH:19]=2)=[N:34][N:33]=1)[CH3:31]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 79890PropionylhydrazineHCID 13633435N-(4-methoxyphenyl)-4-nitro-3-methylbenzene carboximidoyl chloride

Product 1

HCID 191052393-ethyl-4-(4-methoxyphenyl)-5-(4-nitro-3-methylphenyl)-4H-1,2,4-triazoleYield 90.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 6212ChloroformSolvent

Procedure

1.4 ml of triethylamine, then 3 g of the product of Step B were introduced into a solution of 1.76 g of propionic acid hydrazide in 160 ml of toluene, this latter having been brought to reflux and then cooled. After refluxing for 1 hour, the toluene was eliminated under reduced pressure and the residue was taken up in 50 ml of chloroform and 50 ml of water. The aqueous phase was extracted with chloroform and the organic extracts were dried and concentrated to obtain an oil which was purified by chromatography on silica and elution with ethyl acetate and cyclohexane (8-2) to obtain 3 g of 3-ethyl-4-(4-methoxyphenyl)-5-(4-nitro-3-methylphenyl)-4H-1,2,4-triazole in the form of an oil which had an Rf of 0.6 on thin film chromatography (eluent:chloroformethanol 9-1).

Workup

  1. temperatureto reflux
  2. temperaturecooled
  3. temperatureAfter refluxing for 1 hour
  4. extractionThe aqueous phase was extracted with chloroform
  5. customthe organic extracts were dried
  6. concentrationconcentrated
  7. customto obtain an oil which
  8. customwas purified by chromatography on silica and elution with ethyl acetate and cyclohexane (8-2)

Sources & evidence

ORD record
ord-e7abdfbe1afa475bad383ea23d5f7867
Source dataset
uspto-grants-1994_01
Patent number
US05278180

Linked notes

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