Carbon Tetrachloride → HCID 71073412, compound

HRID 1479133Notes

Reaction equation

HRID 1479133 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]1([CH:36]=[CH:35][CH:34]=[CH:33][CH2:32]1)[CH:27]=[N:28][C:29](=O)[CH3:30])C>O>[CH3:30][C:29]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:10])[N:9]=[C:27]([C:26]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:28]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 86674301HCID 86674301, compound

Product 1

HCID 71073412HCID 71073412, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Next, 9.1 g of o-tolyl hydrazine hydrochloride and 100 mL of carbon tetrachloride were put into a 300-mL three-neck flask, 12 mL of triethylamine (Et3N) was added dropwise to the mixture little by little, and the mixture was stirred at room temperature for 1 hour. After a predetermined time elapsed, 10 g of N-(1-ethoxybenzylidene)acetamide was added, and the mixture was stirred at room temperature for 19 hours. Then, water was added to this reacted solution and the aqueous layer was subjected to extraction with chloroform. The obtained solution of the extract and the organic layer were combined and washed with saturated saline, and anhydrous magnesium sulfate was added to the organic layer for drying. 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. As the developing solvent, dichloromethane was used. The obtained fraction was concentrated, so that 5-methyl-1-(2-methylphenyl)-3-phenyl-1H-1,2,4-triazole (abbreviation: HMp3tz1-mp) was obtained (a red oily substance, 64% yield). The synthesis scheme of Step 2 is shown in (B-2) below.

Workup

  1. stirringthe mixture was stirred at room temperature for 19 hours
  2. extractionthe aqueous layer was subjected to extraction with chloroform
  3. extractionThe obtained solution of the extract
  4. washwashed with saturated saline, and anhydrous magnesium sulfate
  5. additionwas added to the organic layer
  6. customfor drying
  7. filtrationThe obtained mixture was gravity-filtered
  8. concentrationthe filtrate was concentrated
  9. customto give an oily substance
  10. customThe obtained oily substance was purified by silica gel column chromatography
  11. concentrationThe obtained fraction was concentrated, so that 5-methyl-1-(2-methylphenyl)-3-phenyl-1H-1,2,4-triazole (abbreviation: HMp3tz1-mp)
  12. customwas obtained (a red oily substance, 64% yield)
  13. customThe synthesis scheme of Step 2

Sources & evidence

ORD record
ord-720b5da520e24d11bc3c9c50d418f1b9
Source dataset
uspto-grants-2016_08
Patent number
US09406894B2

Reaction notes

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