Carbon Tetrachloride → HCID 71073515, compound

HRID 1479131Notes

Reaction equation

HRID 1479131 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:38]=[CH:37][CH:36]=[CH:35][CH2:34]1)[CH:27]=[N:28][C:29](=O)[CH2:30][CH2:31][CH3:32])C>C(Cl)(Cl)Cl>[CH3:10][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:29]([CH2:30][CH2:31][CH3:32])=[N:28][C:27]([C:26]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[N:9]1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 71073554HCID 71073554, compound

Product 1

HCID 71073515HCID 71073515, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Next, 8.1 g of o-tolyl hydrazine hydrochloride and 100 mL of carbon tetrachloride were put into a 500-mL three-neck flask, 7.8 g of triethylamine (Et3N) was added dropwise to this mixture little by little, and the mixture was stirred at room temperature for 1 hour. After a predetermined time elapsed, 11 g of N-(1-ethoxybenzylidene)butyramide obtained in Step 1 was added to the mixture, and the mixture was stirred at room temperature for 24 hours. After the stirring, the mixture was dissolved in chloroform and washed with water and saturated saline. After the washing, anhydrous magnesium sulfate was added to the organic layer for drying. This mixture was gravity-filtered, and the obtained filtrate was concentrated to give an oily substance. This oily substance was purified by silica gel column chromatography. As the developing solvent, a mixed solvent of dichloromethane and ethyl acetate in a ratio of 24:1 (v/v) was used. The obtained fraction was concentrated, so that 1-(2-methylphenyl)-3-phenyl-5-propyl-1H-1,2,4-triazole (abbreviation: HPrp3tz1-mp) was obtained (a red oily substance, 45% yield). The synthesis scheme of Step 2 is shown in (A-2) below.

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. washwashed with water and saturated saline
  3. additionAfter the washing, anhydrous magnesium sulfate was added to the organic layer
  4. customfor drying
  5. filtrationThis mixture was gravity-filtered
  6. concentrationthe obtained filtrate was concentrated
  7. customto give an oily substance
  8. customThis oily substance was purified by silica gel column chromatography
  9. concentrationThe obtained fraction was concentrated, so that 1-(2-methylphenyl)-3-phenyl-5-propyl-1H-1,2,4-triazole (abbreviation: HPrp3tz1-mp)
  10. customwas obtained (a red oily substance, 45% yield)
  11. customThe synthesis scheme of Step 2

Sources & evidence

ORD record
ord-573bd8ed2882458aa4c0feb2bf23572c
Source dataset
uspto-grants-2016_08
Patent number
US09406894B2

Reaction notes

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