Carbon Tetrachloride → HCID 71073526, compound

HRID 1479137Notes

Reaction equation

HRID 1479137 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]=[C:35]([Br:39])[CH2:34]1)[CH:27]=[N:28][C:29](=O)[CH2:30][CH2:31][CH3:32])C>O>[Br:39][C:35]1[CH:34]=[C:26]([C:27]2[N:28]=[C:29]([CH2:30][CH2:31][CH3:32])[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:10])[N:9]=2)[CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 71073607HCID 71073607, compound

Product 1

HCID 71073526HCID 71073526, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Next, 6.5 g of o-tolyl hydrazine hydrochloride and 100 mL of carbon tetrachloride were put into a 200-mL three-neck flask, 4.1 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, 12 g of N-(1-ethoxy-3-bromobenzylidene)butyramide obtained in Step 1 above was added to the mixture, and the mixture was stirred at room temperature for 48 hours. After the reaction, water was added to the reaction mixture and the aqueous layer was subjected to extraction with chloroform. The organic layer and the obtained solution of the extract were combined and washed with water and saturated saline. Anhydrous magnesium sulfate was added to the organic layer for drying and the obtained mixture was concentrated to give an oily substance. The obtained oily substance was purified by flash column chromatography. As the developing solvent, a mixed solvent of hexane and ethyl acetate in a ratio of 5:1 (v/v) was used. The obtained fraction was concentrated to give 3-(3-bromophenyl)-1-(2-methylphenyl)-5-propyl-1H-1,2,4-triazole (a red oily substance, 80% yield). The synthesis scheme of Step 2 is shown in (G-2) below.

Workup

  1. stirringthe mixture was stirred at room temperature for 48 hours
  2. additionwas added to the reaction mixture
  3. extractionthe aqueous layer was subjected to extraction with chloroform
  4. washwashed with water and saturated saline
  5. additionAnhydrous magnesium sulfate was added to the organic layer
  6. customfor drying
  7. concentrationthe obtained mixture was concentrated
  8. customto give an oily substance
  9. customThe obtained oily substance was purified by flash column chromatography
  10. concentrationThe obtained fraction was concentrated

Sources & evidence

ORD record
ord-d6a116ff855f4dcdbaa08eff106ca235
Source dataset
uspto-grants-2016_08
Patent number
US09406894B2

Reaction notes

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