Carbon Tetrachloride → 3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole

HRID 573394

Reaction equation

HRID 573394 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][NH2:9].C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C.C(O[C:26](=[N:28][C:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:27])C>O>[CH3:27][C:26]1[N:28]=[C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:10])[N:9]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 13028604Ethyl (1E)-N-benzoylethanimidate

Product 1

HCID 580684593-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazoleYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Next, into a 300-mL recovery flask were put 8.68 g of o-tolylhydrazine hydrochloride, 100 mL of carbon tetrachloride, and 35 mL of triethylamine (Et3N), and the mixture was stirred at room temperature for 1 hour. After a predetermined time elapsed, 8.72 g of N-(1-ethoxyethylidene)benzamide obtained in Step 1 above was added to this mixture, and the mixture was stirred at room temperature for 24 hours. After a predetermined time elapsed, water was added to the reaction mixture, and the aqueous layer was subjected to extraction with chloroform. The organic layer was washed with saturated brine, and dried with anhydrous magnesium sulfate added thereto. The obtained mixture was gravity-filtered, and the filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography. Dichloromethane was used as a developing solvent. The obtained fraction was concentrated to give 3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole (abbreviation: HMptzl-mp) (an orange oily substance, 84% yield). A synthesis scheme of Step 2 is shown in (a-2) below

Workup

  1. customNext, into a 300-mL recovery flask were put
  2. extractionthe aqueous layer was subjected to extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. additionadded
  6. filtrationThe obtained mixture was gravity-filtered
  7. concentrationthe filtrate was concentrated
  8. customto give an oily substance
  9. customThe obtained oily substance was purified by silica gel column chromatography
  10. concentrationThe obtained fraction was concentrated

Sources & evidence

ORD record
ord-ddd45484f0914af79feb01ae0ca144cc
Source dataset
uspto-grants-2015_05
Patent number
US09029558B2

Linked notes

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