(2,4,6-Trichlorophenyl)hydrazine → HCID 54257533, compound

HRID 1378647Notes

Reaction equation

HRID 1378647 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]([C:12]#[N:13])=[C:5]([O:9][CH2:10][CH3:11])OCC.[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[C:17]=1[NH:24][NH2:25]>C(O)C>[CH3:1][O:2][C:3]([C:4]1[C:5]([O:9][CH2:10][CH3:11])=[N:25][N:24]([C:17]2[C:18]([Cl:23])=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=2[Cl:15])[C:12]=1[NH2:13])=[O:14]

Participants

4

Reactant 2

HCID 79234(2,4,6-Trichlorophenyl)hydrazineHCID 54189837HCID 54189837, compound

Product 1

HCID 54257533HCID 54257533, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude product obtained in Step A (4.76 g, containing approximately 1.9 g, 9.6 mmol of 2-cyano-3,3-diethoxy-acrylic acid methyl ester) was combined with 2,4,6-trichlorophenylhydrazine (2.02 g, 9.6 mmol) in ethanol (15 ml). The resulting mixture was refluxed for 18 hours. The solvent was removed in vacuo, and the residue was extracted with methylene chloride/water (100 ml of each) with the pH adjusted to 10 with sodium carbonate. The separated aqueous extract was washed with two 50 ml portions of methylene chloride. The three combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to an oil (5.98 g). The purity of this crude title compound was significantly improved by flash chromatography (silica gel, 40 micron mesh; elution with ethyl acetate/hexane=15:85 in volume), yielding 910 mg of the title compound as an orange oil. TLC Rf (silica gel plates, u.v. detection; ethyl acetate hexane=15.85 in volume): 0.26. The product was used in the next step without further purification.

Workup

  1. temperatureThe resulting mixture was refluxed for 18 hours
  2. customThe solvent was removed in vacuo
  3. extractionthe residue was extracted with methylene chloride/water (100 ml of each) with the pH
  4. extractionThe separated aqueous extract
  5. washwas washed with two 50 ml portions of methylene chloride
  6. dry with materialThe three combined organic extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo to an oil (5.98 g)
  8. washThe purity of this crude title compound was significantly improved by flash chromatography (silica gel, 40 micron mesh; elution with ethyl acetate/hexane=15:85 in volume)

Sources & evidence

ORD record
ord-2ad5474423704e02845a9558cb449db1
Source dataset
uspto-grants-1997_09
Patent number
US05668145

Reaction notes

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